Liquid crystal composition and liquid crystal display device

ABSTRACT

Shown are a liquid crystal composition satisfying at least one of characteristics such as high maximum temperature, low minimum temperature, low viscosity, suitable optical anisotropy and large negative dielectric anisotropy, or having a suitable balance regarding at least two of the characteristics, and an AM device including the composition. The liquid crystal composition contains a specific compound having large negative dielectric anisotropy as a first component, and a specific compound having low viscosity as a second component, and may contain a specific compound having negative dielectric anisotropy as a third component, a specific compound having high maximum temperature or low viscosity as a fourth component, or a specific compound having a polymerizable group as an additive.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims the priority benefits of Japan applicationserial no. 2017-034601, filed on Feb. 27, 2017, and Japan applicationserial no. 2017-084159, filed on Apr. 21, 2017. The entirety of theabove-mentioned patent applications is hereby incorporated by referenceherein and made apart of this specification.

TECHNICAL FIELD

The invention relates to a liquid crystal composition, a liquid crystaldisplay device including the composition, and so forth. In particular,the invention relates to a liquid crystal composition having negativedielectric anisotropy, and a liquid crystal display device that includesthe composition and has a mode such as an IPS mode, a VA mode, an FFSmode and an FPA mode. The invention also relates to a polymer sustainedalignment mode liquid crystal display device.

BACKGROUND ART

In a liquid crystal display device, a classification based on anoperating mode for liquid crystal molecules includes a phase change (PC)mode, a twisted nematic (TN) mode, a super twisted nematic (STN) mode,an electrically controlled birefringence (ECB) mode, an opticallycompensated bend (OCB) mode, an in-plane switching (IPS) mode, avertical alignment (VA) mode, a fringe field switching (FFS) mode and afield-induced photo-reactive alignment (FPA) mode. A classificationbased on a driving mode in the device includes a passive matrix (PM) andan active matrix (AM). The PM is classified into static, multiplex andso forth, and the AM is classified into a thin film transistor (TFT), ametal insulator metal (MIM) and so forth. The TFT is further classifiedinto amorphous silicon and polycrystal silicon. The latter is classifiedinto a high temperature type and a low temperature type based on aproduction process. A classification based on a light source includes areflective type utilizing natural light, a transmissive type utilizingbacklight and a transflective type utilizing both the natural light andthe backlight.

The liquid crystal display device includes a liquid crystal compositionhaving a nematic phase. The composition has suitable characteristics. AnAM device having good characteristics can be obtained by improvingcharacteristics of the composition. Table 1 below summarizes arelationship in the characteristics. The characteristics of thecomposition will be further described based on a commercially availableAM device. A temperature range of the nematic phase relates to atemperature range in which the device can be used. A preferred maximumtemperature of the nematic phase is about 70° C. or higher, and apreferred minimum temperature of the nematic phase is about −10° C. orlower. Viscosity of the composition relates to a response time in thedevice. A short response time is preferred for displaying moving imageson the device. A shorter response time even by one millisecond isdesirable. Accordingly, a low viscosity in the composition is preferred.A low viscosity at low temperature is further preferred.

TABLE 1 Characteristics of composition and characteristics of AM deviceNo. Characteristics of composition Characteristics of AM device 1 Widetemperature range of a Wide usable temperature range nematic phase 2 Lowviscosity Short response time 3 Suitable optical anisotropy Largecontrast ratio 4 Large positive or negative Low threshold voltage anddielectric anisotropy small electric power consumption Large contrastratio 5 Large specific resistance Large voltage holding ratio and largecontrast ratio 6 High stability to ultraviolet light Long service lifeand heat

Optical anisotropy of the composition relates to a contrast ratio in thedevice. According to a mode of the device, large optical anisotropy orsmall optical anisotropy, more specifically, suitable optical anisotropyis required. A product (Δn×d) of the optical anisotropy (Δn) of thecomposition and a cell gap (d) in the device is designed so as tomaximize the contrast ratio. A suitable value of the product depends ona type of the operating mode. In a device having the VA mode, the valueis in the range from about 0.30 micrometer to about 0.40 micrometer, andin a device having the IPS mode or the FFS mode, the value is in therange from about 0.20 micrometer to about 0.30 micrometer. In the abovecase, a composition having large optical anisotropy is preferred for adevice having a small cell gap. Large dielectric anisotropy in thecomposition contributes to low threshold voltage, small electric powerconsumption and a large contrast ratio in the device. Accordingly, thelarge dielectric anisotropy is preferred. Large specific resistance inthe composition contributes to a large voltage holding ratio and thelarge contrast ratio in the device. Accordingly, a composition havinglarge specific resistance in an initial stage is preferred. Thecomposition having the large specific resistance even after the devicehas been used for a long period of time is preferred. Stability of thecomposition to ultraviolet light or heat relates to a service life ofthe device. In the case where the stability is high, the device has along service life. Such characteristics are preferred for an AM deviceuse in a liquid crystal monitor, a liquid crystal television and soforth.

In a general-purpose liquid crystal display device, vertical alignmentof liquid crystal molecules is achieved by a specific polyimidealignment film. In a polymer sustained alignment (PSA) mode liquidcrystal display device, a polymer is combined with an alignment film.First, a composition to which a small amount of a polymerizable compoundis added is injected into the device. Next, the composition isirradiated with ultraviolet light while voltage is applied betweensubstrates of the device. The polymerizable compound is polymerized toform a network structure of the polymer in the composition. In thecomposition, alignment of liquid crystal molecules can be controlled bythe polymer, and therefore the response time in the device is shortenedand also image persistence is improved. Such an effect of the polymercan be expected for a device having the mode such as the TN mode, theECB mode, the OCB mode, the IPS mode, the VA mode, the FFS mode and theFPA mode.

A composition having positive dielectric anisotropy is used in an AMdevice having the TN mode. A composition having negative dielectricanisotropy is used in an AM device having the VA mode. In an AM devicehaving the IPS mode or the FFS mode, a composition having positive ornegative dielectric anisotropy is used. In a polymer sustained alignmentmode AM device, a composition having positive or negative dielectricanisotropy is used. A compound contained in a first component of theinvention is disclosed in Patent literature No. 1 described below.

CITATION LIST Patent Literature

Patent literature No. 1: WO 2009/125668 A1.

SUMMARY OF INVENTION Technical Problem

The invention provides a liquid crystal composition satisfying at leastone of characteristics such as high maximum temperature of a nematicphase, low minimum temperature of the nematic phase, low viscosity,suitable optical anisotropy, large negative dielectric anisotropy, largespecific resistance, high stability to ultraviolet light and highstability to heat. The invention further provides a liquid crystalcomposition having a suitable balance regarding at least two of thecharacteristics. The invention also provides a liquid crystal displaydevice including such a composition. The invention still furtherprovides an AM device having characteristics such as a short responsetime, a large voltage holding ratio, low threshold voltage, a largecontrast ratio and a long service life.

Solution to Problem

The invention concerns a liquid crystal composition that has negativedielectric anisotropy, and contains at least one compound selected fromcompounds represented by formula (1) as a first component and at leastone compound selected from compounds represented by formula (2) as asecond component, and a liquid crystal display device including thecomposition:

wherein, in formula (1) and formula (2), R¹ and R² are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, or alkylhaving 1 to 12 carbons in which at least one hydrogen is replaced byfluorine or chlorine; R³ is alkyl having 1 to 12 carbons, alkenyl having2 to 12 carbons, or alkenyl having 2 to 12 carbons in which at least onehydrogen is replaced by fluorine or chlorine; R⁴ is alkenyl having 2 to12 carbons, or alkenyl having 2 to 12 carbons in which at least onehydrogen is replaced by fluorine or chlorine; ring A is1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene,2,3-difluoro-1,4-phenylene, tetrahydropyran-2,5-diyl,pyrimidine-2,5-diyl or pyridine-2,5-diyl; L¹, L², L³ and L⁴ areindependently hydrogen or fluorine, in which at least three thereof isfluorine; and Z¹ is a single bond, ethylene, carbonyloxy ormethyleneoxy.

Advantageous Effects of Invention

One of advantages of the invention is to provide a liquid crystalcomposition satisfying at least one of characteristics such as highmaximum temperature of a nematic phase, low minimum temperature of thenematic phase, low viscosity, suitable optical anisotropy, largenegative dielectric anisotropy, large specific resistance, highstability to ultraviolet light and high stability to heat. Anotheradvantage is to provide a liquid crystal composition having a suitablebalance regarding at least two of the characteristics. Another advantageis to provide a liquid crystal display device including such acomposition. Another advantage is to provide an AM device havingcharacteristics such as a short response time, a large voltage holdingratio, low threshold voltage, a large contrast ratio and a long servicelife.

DESCRIPTION OF EMBODIMENTS

Usage of terms herein is as described below. Terms “liquid crystalcomposition” and “liquid crystal display device” may be occasionallyabbreviated as “composition” and “device,” respectively. “Liquid crystaldisplay device” is a generic term for a liquid crystal display panel anda liquid crystal display module. “Liquid crystal compound” is a genericterm for a compound having a liquid crystal phase such as a nematicphase and a smectic phase, and a compound having no liquid crystal phasebut to be mixed with the composition for the purpose of adjustingcharacteristics such as a temperature range of the nematic phase,viscosity and dielectric anisotropy. The compound has a six-memberedring such as 1,4-cyclohexylene or 1,4-phenylene, and has rod-likemolecular structure. “Polymerizable compound” is a compound to be addedfor the purpose of forming a polymer in the composition. A liquidcrystal compound having alkenyl is not polymerizable in the abovemeaning.

The liquid crystal composition is prepared by mixing a plurality ofliquid crystal compounds. An additive such as an optically activecompound, an antioxidant, an ultraviolet light absorber, a dye, anantifoaming agent, the polymerizable compound, a polymerizationinitiator, a polymerization inhibitor and a polar compound is added tothe liquid crystal composition when necessary. A proportion of theliquid crystal compound is expressed in terms of weight percent (% byweight) based on the weight of the liquid crystal composition containingno additive even after the additive has been added. A proportion of theadditive is expressed in terms of weight percent (% by weight) based onthe weight of the liquid crystal composition containing no additive.More specifically, a proportion of the liquid crystal compound or theadditive is calculated based on the total weight of the liquid crystalcompound. Weight parts per million (ppm) may be occasionally used. Aproportion of the polymerization initiator and the polymerizationinhibitor is exceptionally expressed based on the weight of thepolymerizable compound.

“Maximum temperature of the nematic phase” may be occasionallyabbreviated as “maximum temperature.” “Minimum temperature of thenematic phase” may be occasionally abbreviated as “minimum temperature.”An expression “having large specific resistance” means that thecomposition has large specific resistance in an initial stage, and thecomposition has the large specific resistance even after the device hasbeen used for a long period of time. An expression “having a largevoltage holding ratio” means that the device has a large voltage holdingratio at room temperature and also at a temperature close to the maximumtemperature in an initial stage, and the device has the large voltageholding ratio at room temperature and also at a temperature close to themaximum temperature even after the device has been used for a longperiod of time. Characteristics of the composition or the device may beoccasionally examined by an aging test. An expression “increase thedielectric anisotropy” means that a value of dielectric anisotropypositively increases in a composition having positive dielectricanisotropy, and the value of dielectric anisotropy negatively increasesin a composition having negative dielectric anisotropy.

A compound represented by formula (1) may be occasionally abbreviated as“compound (1).” At least one compound selected from the group ofcompounds represented by formula (1) may be occasionally abbreviated as“compound (1).” “Compound (1)” means one compound, a mixture of twocompounds or a mixture of three or more compounds represented by formula(1). A same rule applies also to any other compound represented by anyother formula. An expression “at least one piece of ‘A’” means that thenumber of ‘A’ is arbitrary. An expression “at least one piece of ‘A’ maybe replaced by ‘B’” means that, when the number of ‘A’ is 1, a positionof ‘A’ is arbitrary, and also when the number of ‘A’ is 2 or more,positions thereof can be selected without restriction. A same ruleapplies also to an expression “at least one piece of ‘A’ is replaced by‘B’.”

An expression such as “at least one piece of —CH₂— may be replaced by—O—” is used herein. In the above case, —CH₂—CH₂—CH₂— may be convertedinto —O—CH₂—O— by replacement of non-adjacent —CH₂— by —O—. However, acase where —CH₂— adjacent to each other is replaced by —O— is excluded.The reason is that —O—O—CH₂— (peroxide) is formed in the abovereplacement. More specifically, the expression means both “one piece of—CH₂— may be replaced by —O—” and “at least two pieces of non-adjacent—CH₂— may be replaced by —O—.” A same rule applies not only toreplacement to —O— but also to replacement to a divalent group such as—CH═CH— or —COO—.

A symbol of terminal group R¹ is used in a plurality of compounds inchemical formulas of component compounds. In the compounds, two groupsrepresented by two pieces of arbitrary R¹ may be identical or different.For example, in one case, R¹ of compound (1-1) is ethyl and R¹ ofcompound (1-2) is ethyl. In another case, R¹ of compound (1-1) is ethyland R¹ of compound (1-2) is propyl. A same rule applies also to a symbolof any other terminal group or the like. In formula (3), when asubscript ‘a’ is 2, two of ring B exists. In the compound, two ringsrepresented by two of ring B may be identical or different. A same ruleapplies also to two of arbitrary ring B when the subscript ‘a’ is largerthan 2. A same rule applies also to a symbol of Z⁴, ring I or the like.A same rule applies also to such a case where two pieces of -Sp²-P²exists in compound (5-27).

Symbol A, B, C, D or the like surrounded by a hexagonal shapecorresponds to ring A, ring B, ring C and ring D, respectively, andrepresents a six-membered ring, a fused ring or the like. In compound(5), an oblique line crossing one side of the hexagonal shape representsthat arbitrary hydrogen on the ring may be replaced by -Sp¹-P¹ group orthe like. A subscript such as ‘e’ represents the number of groups to bereplaced. When the subscript ‘e’ is 0 (zero), no such replacementexists. When the subscript ‘e’ is 2 or more, a plurality of pieces of-Sp¹-P¹- exist on ring G. The plurality of groups represented by -Sp¹-P¹may be identical or different. In an expression “ring A and ring B areindependently X, Y or Z,” the subject is plural, and therefore“independently” is used. When the subject is “ring A,” the subject issingular, and therefore “independently” is not used.

Then, 2-fluoro-1,4-phenylene means two divalent groups described below.In a chemical formula, fluorine may be leftward (L) or rightward (R). Asame rule applies also to a left-right asymmetrical divalent groupformed by removing two hydrogens from tetrahydropyran-2,5-diyl or aring. A same rule applies also to a divalent bonding group such ascarbonyloxy (—COO— or —OCO—).

Alkyl of the liquid crystal compound is straight-chain alkyl orbranched-chain alkyl, and includes no cyclic alkyl. Straight-chain alkylis preferred to branched-chain alkyl. A same rule applies also to aterminal group such as alkoxy and alkenyl. With regard to aconfiguration of 1,4-cyclohexylene, trans is preferred to cis forincreasing the maximum temperature.

The invention includes items described below.

Item 1. A liquid crystal composition that has negative dielectricanisotropy, and contains at least one compound selected from compoundsrepresented by formula (1) as a first component and at least onecompound selected from compounds represented by formula (2) as a secondcomponent:

wherein, in formula (1) and formula (2), R¹ and R² are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, or alkylhaving 1 to 12 carbons in which at least one hydrogen is replaced byfluorine or chlorine; R³ is alkyl having 1 to 12 carbons, alkenyl having2 to 12 carbons, or alkenyl having 2 to 12 carbons in which at least onehydrogen is replaced by fluorine or chlorine; R⁴ is alkenyl having 2 to12 carbons, or alkenyl having 2 to 12 carbons in which at least onehydrogen is replaced by fluorine or chlorine; ring A is1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene,2,3-difluoro-1,4-phenylene, tetrahydropyran-2,5-diyl,pyrimidine-2,5-diyl or pyridine-2,5-diyl; L¹, L², L³ and L⁴ areindependently hydrogen or fluorine, in which at least three thereof isfluorine; and Z¹ is a single bond, ethylene, carbonyloxy ormethyleneoxy.

Item 2. The liquid crystal composition according to item 1, containingat least one compound selected from the group of compounds representedby formula (1-1) to formula (1-8) as the first component:

wherein, in formula (1-1) to formula (1-8), R¹ and R² are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, or alkylhaving 1 to 12 carbons in which at least one hydrogen is replaced byfluorine or chlorine.

Item 3. The liquid crystal composition according to item 1 or 2,containing at least one compound selected from the group of compoundsrepresented by formula (2-1) to formula (2-18) as the second component:

Item 4. The liquid crystal composition according to any one of items 1to 3, wherein a proportion of the first component is in the range from3% by weight to 25% by weight, and a proportion of the second componentis in the range from 15% by weight to 70% by weight, based on the weightof the liquid crystal composition.

Item 5. The liquid crystal composition according to any one of items 1to 4, containing at least one compound selected from compoundsrepresented by formula (3) as a third component:

wherein, in formula (3), R⁵ and R⁶ are independently alkyl having 1 to12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkenyloxy having 2 to 12 carbons, or alkyl having 1 to 12carbons in which at least one hydrogen is replaced by fluorine orchlorine; ring B and ring D are independently 1,4-cyclohexylene,1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl,1,4-phenylene in which at least one hydrogen is replaced by fluorine orchlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl in which at leastone hydrogen is replaced by fluorine or chlorine, chroman-2,6-diyl, orchroman-2,6-diyl in which at least one hydrogen is replaced by fluorineor chlorine; ring C is 2,3-difluoro-1,4-phenylene,2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene,3,4,5-trifluoronaphthalene-2,6-diyl or 7,8-difluorochroman-2,6-diyl; Z²and Z³ are independently a single bond, ethylene, carbonyloxy ormethyleneoxy; and a is 1, 2 or 3, b is 0 or 1, and a sum of a and b is 3or less; however compounds represented by formula (1) are excluded fromcompounds represented by formula (3):

wherein, in formula (1), R¹ and R² are independently alkyl having 1 to12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkenyloxy having 2 to 12 carbons, or alkyl having 1 to 12carbons in which at least one hydrogen is replaced by fluorine orchlorine; ring A is 1,4-cyclohexylene, 1,4-phenylene,2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene,tetrahydropyran-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl; L¹,L², L³ and L⁴ are independently hydrogen or fluorine, in which at leastthree thereof is fluorine; and Z¹ is a single bond, ethylene,carbonyloxy or methyleneoxy.

Item 6. The liquid crystal composition according to anyone of items 1 to5, containing at least one compound selected from the group of compoundsrepresented by formula (3-1) to formula (3-22) as the third component:

wherein, in formula (3-1) to formula (3-22), R⁵ and R⁶ are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, or alkylhaving 1 to 12 carbons in which at least one hydrogen is replaced byfluorine or chlorine.

Item 7. The liquid crystal composition according to item 5 or 6, whereina proportion of the third component is in the range from 20% by weightto 75% by weight based on the weight of the liquid crystal composition.

Item 8. The liquid crystal composition according to any one of items 1to 7, containing at least one compound selected from compoundsrepresented by formula (4) as a fourth component:

wherein, in formula (4), R⁷ and R⁸ are independently alkyl having 1 to12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkyl having 1 to 12 carbons in which at least one hydrogen isreplaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons inwhich at least one hydrogen is replaced by fluorine or chlorine; ring Eand ring F are independently 1,4-cyclohexylene, 1,4-phenylene,2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; Z⁴ is a singlebond, ethylene or carbonyloxy; c is 1, 2 or 3; and ring F is1,4-phenylene when c is 1.

Item 9. The liquid crystal composition according to any one of items 1to 8, containing at least one compound selected from the group ofcompounds represented by formula (4-1) to formula (4-12) as the fourthcomponent:

wherein, in formula (4-1) to formula (4-12), R⁷ and R⁸ are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkyl having 1 to 12 carbons in which at leastone hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to12 carbons in which at least one hydrogen is replaced by fluorine orchlorine.

Item 10. The liquid crystal composition according to item 8 or 9,wherein a proportion of the fourth component is in the range from 2°, byweight to 30% by weight based on the weight of the liquid crystalcomposition.

Item 11. The liquid crystal composition according to any one of items 1to 10, containing at least one compound selected from polymerizablecompounds represented by formula (5) as an additive:

wherein, in formula (5), ring G and ring J are independently cyclohexyl,cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl,1,3-dioxane-2-yl, pyrimidine-2-yl or pyridine-2-yl, and in these rings,at least one hydrogen may be replaced by fluorine, chlorine, alkylhaving 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1to 12 carbons in which at least one hydrogen is replaced by fluorine orchlorine; ring I is 1,4-cyclohexylene, 1,4-cyclohexenylene,1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl,naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl,naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl,naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl,1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, and inthese rings, at least one hydrogen may be replaced by fluorine,chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons,or alkyl having 1 to 12 carbons in which at least one hydrogen isreplaced by fluorine or chlorine; Z⁵ and Z⁶ are independently a singlebond or alkylene having 1 to 10 carbons, and in the alkylene, at leastone piece of —CH₂— may be replaced by —O—, —CO—, —COO— or —OCO—, and atleast one piece of —CH₂—CH₂— may be replaced by —CH═CH—, —C(CH₃)═CH—,—CH═C(CH₃)— or —C(CH₃)═C(CH₃)—, and in these groups, at least onehydrogen may be replaced by fluorine or chlorine; p¹, p² and p³ areindependently a polymerizable group; Sp¹, Sp² and Sp³ are independentlya single bond or alkylene having 1 to 10 carbons, and in the alkylene,at least one piece of —CH₂— may be replaced by —O—, —COO—, —OCO— or—OCOO—, and at least one piece of —CH₂—CH₂— may be replaced by —CH═CH—or —C≡C—, and in these groups, at least one hydrogen may be replaced byfluorine or chlorine; d is 0, 1 or 2; and e, f and g are independently0, 1, 2, 3 or 4, and a sum of e, f and g is 1 or more.

Item 12. The liquid crystal composition according to item 11, wherein,in formula (5), p¹, p² and p³ are independently a group selected fromthe group of polymerizable groups represented by formula (P-1) toformula (P-5):

wherein, in formula (P-1) to formula (P-5), M¹, M² and M³ areindependently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkylhaving 1 to 5 carbons in which at least one hydrogen is replaced byfluorine or chlorine.

Item 13. The liquid crystal composition according to any one of items 1to 12, containing at least one compound selected from the group ofpolymerizable compounds represented by formula (5-1) to formula (5-27)as the additive:

wherein, in formula (5-1) to formula (5-27), p¹, p² and p³ areindependently a group selected from the group of polymerizable groupsrepresented by formula (P-1) to formula (P-3):

wherein M¹, M² and M³ are independently hydrogen, fluorine, alkyl having1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least onehydrogen is replaced by fluorine or chlorine; and Sp¹, Sp² and Sp³ areindependently a single bond or alkylene having 1 to 10 carbons, and inthe alkylene, at least one piece of —CH₂— may be replaced by —O—, —COO—,—OCO— or —OCOO—, and at least one piece of —CH₂—CH₂— may be replaced by—CH═CH— or —C≡C—, and in these groups, at least one hydrogen may bereplaced by fluorine or chlorine.

Item 14. The liquid crystal composition according to any of items 11 to13, wherein a proportion of the additive is in the range from 0.03% byweight to 10% by weight based on the weight of the liquid crystalcomposition.

Item 15. A liquid crystal display device, including the liquid crystalcomposition according to any one of items 1 to 14.

Item 16. The liquid crystal display device according to item 15, whereinan operating mode in the liquid crystal display device is an IPS mode, aVA mode, an FFS mode or an FPA mode, and a driving mode in the liquidcrystal display device is an active matrix mode.

Item 17. A polymer sustained alignment mode liquid crystal displaydevice, wherein the liquid crystal display device includes the liquidcrystal composition according to any one of items 1 to 14, and anadditive contained in the liquid crystal composition is polymerized.

Item 18. Use of the liquid crystal composition according to any one ofitems 1 to 14 in a liquid crystal display device.

Item 19. Use of the liquid crystal composition according to any one ofitems 1 to 14 in a polymer sustained alignment mode liquid crystaldisplay device.

The invention further includes the following items: (a) the composition,further containing at least one of additives such as an optically activecompound, an antioxidant, an ultraviolet light absorber, a dye, anantifoaming agent, a polymerizable compound, a polymerization initiator,a polymerization inhibitor and a polar compound; (b) an AM deviceincluding the composition; (c) a polymer sustained alignment (PSA) modeAM device including the composition further containing a polymerizablecompound; (d) the polymer sustained alignment (PSA) mode AM device,wherein the device includes the composition, and the polymerizablecompound in the composition is polymerized; (e) a device including thecomposition and having the PC mode, the TN mode, the STN mode, the ECBmode, the OCB mode, the IPS mode, the VA mode, the FFS mode or the FPAmode; (f) a transmissive device including the composition; (g) use ofthe composition as the composition having the nematic phase; and (h) useas an optically active composition by adding the optically activecompound to the composition.

The composition of the invention will be described in the followingorder. First, a constitution of the composition will be described.Second, main characteristics of the component compounds and main effectsof the compounds on the composition will be described. Third, acombination of components in the composition, a preferred proportion ofthe components and the basis thereof will be described. Fourth, apreferred embodiment of the component compounds will be described.Fifth, a preferred component compound will be described. Sixth, anadditive that may be added to the composition will be described.Seventh, methods for synthesizing the component compounds will bedescribed. Last, an application of the composition will be described.

First, the constitution of the composition will be described. Thecomposition contains a plurality of liquid crystal compounds. Thecomposition may contain an additive. The additive is the opticallyactive compound, the antioxidant, the ultraviolet light absorber, thedye, the antifoaming agent, the polymerizable compound, thepolymerization initiator, the polymerization inhibitor, the polarcompound or the like. The composition is classified into composition Aand composition B from a viewpoint of the liquid crystal compound.Composition A may further contain any other liquid crystal compound, anadditive or the like in addition to the liquid crystal compound selectedfrom compound (1), compound (2), compound (3) and compound (4). “Anyother liquid crystal compound” means a liquid crystal compound differentfrom compound (1), compound (2), compound (3) and compound (4). Such acompound is mixed with the composition for the purpose of furtheradjusting the characteristics.

Composition B consists essentially of liquid crystal compounds selectedfrom compound (1), compound (2), compound (3) and compound (4). The term“essentially” means that the composition may contain the additive, butcontains no any other liquid crystal compound. Composition B has asmaller number of components than composition A has. Composition B ispreferred to composition A in view of cost reduction. Composition A ispreferred to composition B in view of possibility of further adjustingthe characteristics by mixing any other liquid crystal compound.

Second, the main characteristics of the component compounds and the maineffects of the compounds on the composition will be described. The maincharacteristics of the component compounds are summarized in Table 2 onthe basis of advantageous effects of the invention. In Table 2, a symbolL stands for “large” or “high,” a symbol M stands for “medium” and asymbol S stands for “small” or “low.” The symbols L, M and S represent aclassification based on a qualitative comparison among the componentcompounds, and 0 (zero) means that “a value is zero or nearly zero.”

TABLE 2 Characteristics of liquid crystal compounds Compound CompoundCompound Compound Characteristics (1) (2) (3) (4) Maximum M to L M S toL S to L temperature Viscosity M to L S M to L S to M Optical anisotropyM to L S M to L S to L Dielectric anisotropy L¹⁾ 0 M to L¹⁾ 0 Specificresistance L L L L ¹⁾A value of dielectric anisotropy is negative, andthe symbol shows magnitude of an absolute value.

Upon mixing the component compounds with the composition, the maineffects of the component compounds on the characteristics of thecomposition are as described below. Compound (1) increases thedielectric anisotropy. Compound (2) decreases the viscosity. Compound(3) increases the dielectric anisotropy and decreases the minimumtemperature. Compound (4) increases the maximum temperature or decreasesthe viscosity. Compound (5) are polymerized to give a polymer, and thepolymer shortens a response time of the device, and improves imagepersistence.

Third, the combination of components in the composition, a preferredproportion of the components and the basis thereof will be described. Apreferred combination of the components in the composition includes acombination of the first component and the second component, acombination of the first component, the second component and the thirdcomponent, a combination of the first component, the second componentand the fourth component, a combination of the first component, thesecond component and the additive, a combination of the first component,the second component, the third component and the fourth component, acombination of the first component, the second component, the thirdcomponent and the additive, a combination of the first component, thesecond component, the fourth component and the additive, or acombination of the first component, the second component, the thirdcomponent, the fourth component and the additive. A further preferredcombination includes a combination of the first component, the secondcomponent, the third component and the fourth component, or acombination of the first component, the second component, the thirdcomponent, the fourth component and the additive.

A preferred proportion of the first component is about 3% by weight ormore for increasing the dielectric anisotropy, and about 25% by weightor less for decreasing the viscosity. A further preferred proportion isin the range from about 3% by weight to about 20% by weight. Aparticularly preferred proportion is in the range from about 3% byweight to about 15% by weight.

A preferred proportion of the second component is about 15% by weight ormore for decreasing the viscosity, and about 70% by weight or less forincreasing the dielectric anisotropy. A further preferred proportion isin the range from about 15% by weight to about 60% by weight. Aparticularly preferred proportion is in the range from about 20% byweight to about 50% by weight.

A preferred proportion of the third component is about 20% by weight ormore for increasing the dielectric anisotropy, and about 75% by weightor less for decreasing the minimum temperature. A further preferredproportion is in the range from about 25% by weight to about 70% byweight. A particularly preferred proportion is in the range from about30% by weight to about 65% by weight.

A preferred proportion of the fourth component is about 2% by weight ormore for increasing the maximum temperature or decreasing the viscosity,and about 30% by weight or less for increasing the dielectricanisotropy. A further preferred proportion is in the range from about 4%by weight to about 25% by weight. A particularly preferred proportion isin the range from about 4% by weight to about 20% by weight.

An additive is added to the composition for the purpose of adapting thecomposition to the polymer sustained alignment mode device. A preferredproportion of the additive is about 0.03% by weight or more for aligningthe liquid crystal molecules, and about 10% by weight or less forpreventing poor display in the device. A further preferred proportion isin the range from about 0.1% by weight to about 2% by weight. Aparticularly preferred proportion is in the range from about 0.2% byweight to about 1.0% by weight.

Fourth, the preferred embodiment of the component compounds will bedescribed. In formula (1), formula (2), formula (3) and formula (4), R¹,R², R⁵ and R⁶ are independently alkyl having 1 to 12 carbons, alkoxyhaving 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkenyloxyhaving 2 to 12 carbons, or alkyl having 1 to 12 carbons in which atleast one hydrogen is replaced by fluorine or chlorine. Preferred R¹,R², R⁵ or R⁶ is alkyl having 1 to 12 carbons for increasing thestability to ultraviolet light and heat, and alkoxy having 1 to 12carbons for increasing the dielectric anisotropy. R³ is alkyl having 1to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12carbons in which at least one hydrogen is replaced by fluorine orchlorine. Preferred R³ is alkyl having 1 to 12 carbons for increasingthe stability to ultraviolet light and heat, and alkenyl having 2 to 12carbons or alkenyl having 2 to 12 carbons in which at least one hydrogenis replaced by fluorine or chlorine for decreasing the viscosity. R⁴ isalkenyl having 2 to 12 carbons or alkenyl having 2 to 12 carbons inwhich at least one hydrogen is replaced by fluorine or chlorine.Preferred R⁴ is vinyl, 1-propenyl or 2,2-difluorovinyl for decreasingthe viscosity. R⁷ and R⁸ are independently alkyl having 1 to 12 carbons,alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkylhaving 1 to 12 carbons in which at least one hydrogen is replaced byfluorine or chlorine, or alkenyl having 2 to 12 carbons in which atleast one hydrogen is replaced by fluorine or chlorine. Preferred R⁷ orR⁸ is alkenyl having 2 to 12 carbons for decreasing the viscosity, andalkyl having 1 to 12 carbons for increasing the stability to ultravioletlight and heat.

Preferred alkyl is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptylor octyl. Further preferred alkyl is methyl, ethyl, propyl, butyl orpentyl for decreasing the viscosity.

Preferred alkoxy is methoxy, ethoxy, propoxy, butoxy, pentyloxy,hexyloxy or heptyloxy. Further preferred alkoxy is methoxy or ethoxy fordecreasing the viscosity.

Preferred alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl,2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl or 5-hexenyl. Furtherpreferred alkenyl is vinyl, 1-propenyl, 3-butenyl or 3-pentenyl fordecreasing the viscosity. A preferred configuration of —CH═CH— in thealkenyl depends on a position of a double bond. Trans is preferred inalkenyl such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyland 3-hexenyl for decreasing the viscosity, for instance. Cis ispreferred in alkenyl such as 2-butenyl, 2-pentenyl and 2-hexenyl.

Preferred examples of alkyl in which at least one hydrogen is replacedby fluorine or chlorine are fluoromethyl, 2-fluoroethyl, 3-fluoropropyl,4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl, 7-fluoroheptyl or8-fluorooctyl. Further preferred examples are 2-fluoroethyl,3-fluoropropyl, 4-fluorobutyl or 5-fluoropentyl for increasing thedielectric anisotropy.

Preferred examples of alkenyl in which at least one hydrogen is replacedby fluorine or chlorine are 2,2-difluorovinyl, 3,3-difluoro-2-propenyl,4,4-difluoro-3-butenyl, 5,5-difluoro-4-pentenyl or6,6-difluoro-5-hexenyl. Further preferred examples are 2,2-difluorovinylor 4,4-difluoro-3-butenyl for decreasing the viscosity.

Ring A is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene,2,3-difluoro-1,4-phenylene, tetrahydropyran-2,5-diyl,pyrimidine-2,5-diyl or pyridine-2,5-diyl. Preferred ring A is1,4-cyclohexylene for decreasing the viscosity, and 1,4-phenylene forincreasing the optical anisotropy.

Ring B and ring D are independently 1,4-cyclohexylene,1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl,1,4-phenylene in which at least one hydrogen is replaced by fluorine orchlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl in which at leastone hydrogen is replaced by fluorine or chlorine, chroman-2,6-diyl, orchroman-2,6-diyl in which at least one hydrogen is replaced by fluorineor chlorine. Preferred ring B or ring D is 1,4-cyclohexylene fordecreasing the viscosity, tetrahydropyran-2,5-diyl for increasing thedielectric anisotropy, and 1,4-phenylene for increasing the opticalanisotropy. Ring C is 2,3-difluoro-1,4-phenylene,2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene,3,4,5-trifluoronaphthalene-2,6-diyl or 7,8-difluorochroman-2,6-diyl.Preferred ring C is 2,3-difluoro-1,4-phenylene for decreasing theviscosity, 2-chloro-3-fluoro-1,4-phenylene for decreasing the opticalanisotropy, and 7,8-difluorochroman-2,6-diyl for increasing thedielectric anisotropy.

Ring E and ring F are independently 1,4-cyclohexylene, 1,4-phenylene,2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene. Preferred ring Eor ring F is 1,4-cyclohexylene for decreasing the viscosity orincreasing the maximum temperature, and 1,4-phenylene for decreasing theminimum temperature.

Z¹, Z² and Z³ are independently a single bond, ethylene, carbonyloxy ormethyleneoxy. Preferred Z¹ is ethylene or methyleneoxy. Preferred Z² orZ³ is a single bond for decreasing the viscosity, ethylene fordecreasing the minimum temperature, and methyleneoxy for increasing thedielectric anisotropy. Z⁴ is a single bond, ethylene or carbonyloxy.Preferred Z⁴ is a single bond for increasing the stability toultraviolet light and heat.

Then, a is 1, 2 or 3, b is 0 or 1, and a sum of a and b is 3 or less.Preferred a or b is 1 for decreasing the viscosity, and 2 or 3 forincreasing the maximum temperature. Then, c is 1, 2 or 3. Preferred c is1 for decreasing the viscosity, and 2 or 3 for increasing the maximumtemperature.

In formula (5), p¹, p² and p³ are independently a polymerizable group.Preferred p¹, p² or p³ is a group selected from the group ofpolymerizable groups represented by formula (P-1) to formula (P-5).Further preferred p¹, p² or p³ is a group represented by formula (P-1),formula (P-2) or formula (P-3). Particularly preferred p¹, p² or p³ is agroup represented by formula (P-1) or formula (P-2). Most Preferred p¹,p² or p³ is a group represented by formula (P-1). A preferred grouprepresented by formula (P-1) is —OCO—CH═CH₂ or —OCO—C(CH₃)═CH₂. A wavyline in formula (P-1) to formula (P-5) represents a site to formabonding.

In formula (P-1) to formula (P-5), M¹, M² and M³ are independentlyhydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5carbons in which at least one hydrogen is replaced by fluorine orchlorine. Preferred M¹, M² or M³ is hydrogen or methyl for increasingreactivity. Further preferred M¹ is hydrogen or methyl, and furtherpreferred M² or M³ is hydrogen.

Sp¹, Sp² and Sp³ are independently a single bond or alkylene having 1 to10 carbons, and in the alkylene, at least one piece of —CH₂— may bereplaced by —O—, —COO—, —OCO— or —OCOO—, and at least one piece of—CH₂—CH₂— may be replaced by —CH═CH— or —C≡C—, and in these groups, atleast one hydrogen may be replaced by fluorine or chlorine. PreferredSp¹, Sp² or Sp³ is a single bond, —CH₂—CH₂—, —CH₂O—, —OCH₂—, —COO—,—OCO—, —CO—CH═CH— or —CH═CH—CO—. Further preferred Sp¹, Sp² or Sp³ is asingle bond.

Ring G and ring J are independently cyclohexyl, cyclohexenyl, phenyl,1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl,pyrimidine-2-yl or pyridine-2-yl, and in the rings, at least onehydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbonsin which at least one hydrogen is replaced by fluorine or chlorine.Preferred ring G or ring J is phenyl. Ring I is 1,4-cyclohexylene,1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl,naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl,naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl,naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl,tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl orpyridine-2,5-diyl, and in the rings, at least one hydrogen may bereplaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxyhaving 1 to 12 carbons, or alkyl having 1 to 12 carbons in which atleast one hydrogen is replaced by fluorine or chlorine. Preferred ring Iis 1,4-phenylene or 2-fluoro-1,4-phenylene.

Z⁵ and Z⁶ are independently a single bond or alkylene having 1 to 10carbons, and in the alkylene, at least one piece of —CH₂— may bereplaced by —O—, —CO—, —COO— or —OCO—, and at least one piece of—CH₂—CH₂— may be replaced by —CH═CH—, —C(CH₃)═CH—, —CH═C(CH₃)— or—C(CH₃)═C(CH₃)—, and in these groups, at least one hydrogen may bereplaced by fluorine or chlorine. Preferred Z⁵ or Z⁶ is a single bond,—CH₂—CH₂—, —CH₂O—, —OCH₂—, —COO— or —OCO—. Further preferred Z⁵ or Z⁶ isa single bond.

Then, d is 0, 1 or 2. Preferred d is 0 or 1. Then, e, f and g areindependently 0, 1, 2, 3 or 4, and a sum of e, f and g is 1 or more.Preferred e or g is 1 or 2, and preferred f is 0 or 1.

A compound represented by formula (1) and a compound represented byformula (3) are overlapped in several cases. Such a compound is regardedto belong to the compound represented by formula (1). Namely compoundsrepresented by formula (1) are excluded from compounds represented byformula (3):

in which, in formula (1), R¹ and R² are independently alkyl having 1 to12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkenyloxy having 2 to 12 carbons, or alkyl having 1 to 12carbons in which at least one hydrogen is replaced by fluorine orchlorine; ring A is 1,4-cyclohexylene, 1,4-phenylene,2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene,tetrahydropyran-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl; L¹,L², L³ and L⁴ are independently hydrogen or fluorine, in which at leastthree thereof is fluorine; and Z¹ is a single bond, ethylene,carbonyloxy or methyleneoxy.

When the compound represented by formula (4) is a compound having tworings, namely c in the formula is 1, ring F represents 1,4-phenylene.

Fifth, the preferred component compound will be described. Preferredcompound (1) includes compound (1-1) to compound (1-8) described in item2. In the above compounds, at least one of the first componentspreferably includes compound (1-1), compound (1-3) or compound (1-6). Atleast two of the first components preferably includes a combination ofcompound (1-3) and compound (1-6).

Preferred compound (2) includes compound (2-1) to compound (2-18)described in item 3. In the above compounds, at least one of the secondcomponents preferably includes compound (2-1), compound (2-2), compound(2-4), compound (2-5) or compound (2-14). At least two of the secondcomponents preferably includes a combination of compound (2-2) andcompound (2-14).

Preferred compound (3) includes compound (3-1) to compound (3-22)described in item 6. In the above compounds, at least one of the thirdcomponents preferably includes compound (3-1), compound (3-2), compound(3-3), compound (3-4), compound (3-6), compound (3-7), compound (3-8) orcompound (3-10). At least two of the third components preferablyincludes a combination of compound (3-1) and compound (3-6), acombination of compound (3-1) and compound (3-10), a combination ofcompound (3-3) and compound (3-6), a combination of compound (3-3) andcompound (3-10), a combination of compound (3-4) and compound (3-6), ora combination of compound (3-4) and compound (3-10).

Preferred compound (4) includes compound (4-1) to compound (4-12)described in item 9. In the above compounds, at least one of the fourthcomponents preferably includes compound (4-2), compound (4-4), compound(4-5) or compound (4-6). At least two of the fourth componentspreferably includes a combination of compound (4-2) and compound (4-4),or a combination of compound (4-2) and compound (4-6).

Preferred compound (5) includes compound (5-1) to compound (5-27)described in item 13. In the above compounds, at least one of theadditives preferably includes compound (5-1), compound (5-2), compound(5-24), compound (5-25), compound (5-26) or compound (5-27). At leasttwo of the additives preferably includes a combination of compound (5-1)and compound (5-2), a combination of compound (5-1) and compound (5-18),a combination of compound (5-2) and compound (5-24), a combination ofcompound (5-2) and compound (5-25), a combination of compound (5-2) andcompound (5-26), a combination of compound (5-25) and compound (5-26),or a combination of compound (5-18) and compound (5-24).

Sixth, the additive that may be added to the composition will bedescribed. Such an additive includes the optically active compound, theantioxidant, the ultraviolet light absorber, the dye, the antifoamingagent, the polymerizable compound, the polymerization initiator, thepolymerization inhibitor and the polar compound. The optically activecompound is added to the composition for the purpose of inducing ahelical structure in liquid crystal molecules to give a twist angle.Examples of such a compound include compound (6-1) to compound (6-5). Apreferred proportion of the optically active compound is about 5% byweight or less. A further preferred proportion is in the range fromabout 0.01% by weight to about 2% by weight.

The antioxidant is added to the composition for preventing a decrease inthe specific resistance caused by heating in air, or for maintaining alarge voltage holding ratio at room temperature and also at atemperature close to the maximum temperature even after the device hasbeen used for a long period of time. Preferred examples of theantioxidant include compound (7) in which n is an integer from 1 to 9.

In compound (7), preferred n is 1, 3, 5, 7 or 9. Further preferred n is7. Compound (7) in which n is 7 has low volatility, and therefore iseffective in maintaining a large voltage holding ratio at roomtemperature and also at a temperature close to the maximum temperatureeven after the device has been used for a long period of time. Apreferred proportion of the antioxidant is about 50 ppm or more forachieving an effect thereof, and about 600 ppm or less for avoiding adecrease in the maximum temperature or an increase in the minimumtemperature. A further preferred proportion is in the range from about100 ppm to about 300 ppm.

Preferred examples of an ultraviolet light absorber include abenzophenone derivative, a benzoate derivative and a triazolederivative. A light stabilizer such as an amine having steric hindranceis also preferred. A preferred proportion of the absorber or thestabilizer is about 50 ppm or more for achieving an effect thereof, andabout 10,000 ppm or less for avoiding a decrease in the maximumtemperature or an increase in the minimum temperature. A furtherpreferred proportion is in the range from about 100 ppm to about 10,000ppm.

A dichroic dye such as an azo dye or an anthraquinone dye is added tothe composition to be adapted for a device having a guest host (GH)mode. A preferred proportion of the dye is in the range from about 0.01%by weight to about 10% by weight. The antifoaming agent such as dimethylsilicone oil or methyl phenyl silicone oil is added to the compositionfor preventing foam formation. A preferred proportion of the antifoamingagent is about 1 ppm or more for achieving an effect thereof, and about1,000 ppm or less for preventing poor display. A further preferredproportion is in the range from about 1 ppm to about 500 ppm.

The polymerizable compound is used to be adapted for a polymer sustainedalignment (PSA) mode device. Compound (5) is suitable for the purpose.Any other polymerizable compound that is different from compound (5) maybe added to the composition together with compound (5). In place ofcompound (5), any other polymerizable compound that is different fromcompound (5) may be added to the composition. Preferred examples of sucha polymerizable compound include a compound such as acrylate,methacrylate, a vinyl compound, a vinyloxy compound, propenyl ether, anepoxy compound (oxirane, oxetane) and vinyl ketone. Further preferredexamples include an acrylate derivative or a methacrylate derivative.Reactivity of polymerization or a pretilt angle of liquid crystalmolecules can be adjusted by changing a kind of compound (5), or bycombining a polymerizable compound different from compound (5) withcompound (5) at a suitable ratio. The short response time of the devicecan be achieved by optimizing the pretilt angle. Alignment of the liquidcrystal molecules is also stabilized, and therefore a large contrastratio or a long service life can be achieved.

The polymerizable compound is polymerized by irradiation withultraviolet light. The polymerizable compound may be polymerized in thepresence of the initiator such as a photopolymerization initiator.Suitable conditions for polymerization, suitable types of the initiatorand amounts thereof are known to those skilled in the art and aredescribed in literature. For example, Irgacure 651 (registeredtrademark; BASF), Irgacure 184 (registered trademark; BASF) or Darocur1173 (registered trademark; BASF), each being a photoinitiator, issuitable for radical polymerization. A preferred proportion of thephotopolymerization initiator is in the range from about 0.1% by weightto about 5% by weight based on the weight of the polymerizable compound.A further preferred proportion is in the range from about 1% by weightto about 3% by weight.

Upon storing the polymerizable compound, the polymerization inhibitormay be added thereto for preventing polymerization. The polymerizablecompound is ordinarily added to the composition without removing thepolymerization inhibitor. Examples of the polymerization inhibitorinclude hydroquinone, a hydroquinone derivative such asmethylhydroquinone, 4-t-butylcatechol, 4-methoxyphenol andphenothiazine.

The polar compound is an organic compound having polarity. Here, acompound having an ionic bond is not contained. An atom such as oxygen,sulfur and nitrogen is electrically more negative, and tends to have apartial negative charge. Carbon and hydrogen are neutral or tend to havea partial positive charge. The polarity is formed when the partialelectric charge is not uniformly distributed between different kinds ofatoms in the compound. For example, the polar compound has at least oneof partial structures such as —OH, —COOH, —SH, —NH₂, >NH and >N—.

Seventh, the methods for synthesizing the component compounds will bedescribed. The compounds can be prepared according to known methods.Examples of the synthetic methods are described. Compound (1-1) isprepared by the method described in WO 2009/125668 A. Compound (2) isprepared by the method described in JP S59-176221 A or JP H9-77692 A.Compound (3-6) is prepared by the method described in JP 2000-53602 A.Compound (4-2) is prepared by the method described in JP S52-53783 A.Compound (5-18) is prepared by the method described in JP H7-101900 A.The antioxidant is commercially available. A compound in which n informula (7) is 1 is available from Sigma-Aldrich Corporation. Compound(7) in which n is 7 or the like is prepared by a method described inU.S. Pat. No. 3,660,505 B.

Any compounds whose synthetic methods are not described above can beprepared according to methods described in books such as OrganicSyntheses (John Wiley & Sons, Inc.), Organic Reactions (John Wiley &Sons, Inc.), Comprehensive Organic Synthesis (Pergamon Press) and NewExperimental Chemistry Course (Shin Jikken Kagaku Koza in Japanese)(Maruzen Co., Ltd.). The composition is prepared according to publiclyknown methods using the thus obtained compounds. For example, thecomponent compounds are mixed and dissolved in each other by heating.

Last, the application of the composition will be described. Most of thecompositions have a minimum temperature of about −10° C. or lower, amaximum temperature of about 70° C. or higher, and optical anisotropy inthe range from about 0.07 to about 0.20. A composition having opticalanisotropy in the range from about 0.08 to about 0.25 may be prepared bycontrolling a proportion of the component compounds or by mixing anyother liquid crystal compound. Further a composition having opticalanisotropy in the range from about 0.10 to about 0.30 may be prepared bytrial and error. A device including the composition has the largevoltage holding ratio. The composition is suitable for use in the AMdevice. The composition is particularly suitable for use in atransmissive AM device. The composition can be used as the compositionhaving the nematic phase, or as the optically active composition byadding the optically active compound.

The composition can be used in the AM device. The composition can alsobe used in a PM device. The composition can also be used in an AM deviceand a PM device each having a mode such as the PC mode, the TN mode, theSTN mode, the ECB mode, the OCB mode, the IPS mode, the FFS mode, the VAmode and the FPA mode. Use in the AM device having the VA mode, the OCBmode, the IPS mode or the FFS mode is particularly preferred. In the AMdevice having the IPS mode or the FFS mode, alignment of liquid crystalmolecules when no voltage is applied may be parallel or perpendicular toa glass substrate. The devices may be of a reflective type, atransmissive type or a transflective type. Use in the transmissivedevice is preferred. The composition can also be used in an amorphoussilicon-TFT device or a polycrystal silicon-TFT device. The compositioncan also be used in a nematic curvilinear aligned phase (NCAP) deviceprepared by microencapsulating the composition, or a polymer dispersed(PD) device in which a three-dimensional network-polymer is formed inthe composition.

One example of a method for manufacturing the polymer sustainedalignment mode device is as described below. A device having twosubstrates referred to as an array substrate and a color filtersubstrate is assembled. The substrates have an alignment film. At leastone of the substrates has an electrode layer. The liquid crystalcompound is mixed to prepare the liquid crystal composition. Thepolymerizable compound is added to the composition. The additive may befurther added thereto when necessary. The composition is injected intothe device. The device is irradiated with light in a state in whichvoltage is applied thereto. Ultraviolet light is preferred. Thepolymerizable compound is polymerized by irradiation with the light. Thecomposition containing a polymer is formed by the polymerization. Thepolymer sustained alignment mode device is manufactured by such aprocedure.

In the procedure, when voltage is applied, the liquid crystal moleculesare aligned by action of the alignment film and an electric field. Themolecules of the polymerizable compound are also aligned according tothe alignment. The polymerizable compound is polymerized by ultravioletlight in the above state, and therefore the polymer maintaining thealignment is formed. The response time in the device is shortened by aneffect of the polymer. Simultaneously, image persistence is alsoimproved by the effect of the polymer, since the image persistence ispoor operation of liquid crystal molecules. Moreover, the polymerizablecompound in the composition is previously polymerized, and the resultingcomposition can be arranged between the substrates of the liquid crystaldisplay device.

EXAMPLES

The invention will be described in greater detail by way of Examples.However, the invention is not limited by the Examples. The inventionincludes a mixture of a composition in Example 1 and a composition inExample 2. The invention also includes a mixture in which at least twocompositions in Examples are mixed. The thus prepared compound wasidentified by methods such as an NMR analysis. Characteristics of thecompound, the composition and a device were measured by methodsdescribed below.

NMR analysis: For measurement, DRX-500 made by Bruker BioSpinCorporation was used. In ¹H-NMR measurement, a sample was dissolved in adeuterated solvent such as CDCl₃, and measurement was carried out underconditions of room temperature, 500 MHz and 16 times of accumulation.Tetramethylsilane was used as an internal standard. In ¹⁹F-NMRmeasurement, CFCl₃ was used as an internal standard, and measurement wascarried out under conditions of 24 times of accumulation. In explainingnuclear magnetic resonance spectra obtained, s, d, t, q, quin, sex and mstand for a singlet, a doublet, a triplet, a quartet, a quintet, asextet and a multiplet, and br being broad, respectively.

Gas chromatographic analysis: For measurement, GC-14B Gas Chromatographmade by Shimadzu Corporation was used. A carrier gas was helium (2 mLper minute). A sample vaporizing chamber and a detector (FID) were setto 280° C. and 300° C., respectively. A capillary column DB-1 (length 30m, bore 0.32 mm, film thickness 0.25 μm; dimethylpolysiloxane as astationary liquid phase; non-polar) made by Agilent Technologies, Inc.was used for separation of component compounds. After the column waskept at 200° C. for 2 minutes, the column was heated to 280° C. at arate of 5° C. per minute. A sample was prepared in an acetone solution(0.1% by weight), and then 1 microliter of the solution was injectedinto the sample vaporizing chamber. A recorder was C-R5A Chromatopacmade by Shimadzu Corporation or the equivalent thereof. The resultinggas chromatogram showed a retention time of a peak and a peak areacorresponding to each of the component compounds.

As a solvent for diluting the sample, chloroform, hexane or the like mayalso be used. The following capillary columns may also be used forseparating component compounds: HP-1 (length 30 m, bore 0.32 mm, filmthickness 0.25 μm) made by Agilent Technologies, Inc., Rtx-1 (length 30m, bore 0.32 mm, film thickness 0.25 μm) made by Restek Corporation andBP-1 (length 30 m, bore 0.32 mm, film thickness 0.25 μm) made by SGEInternational Pty. Ltd. A capillary column CBP1-M50-025 (length 50 m,bore 0.25 mm, film thickness 0.25 μm) made by Shimadzu Corporation mayalso be used for the purpose of preventing an overlap of peaks of thecompounds.

A proportion of liquid crystal compounds contained in the compositionmay be calculated by the method as described below. The mixture of theliquid crystal compounds is analyzed by gas chromatography (FID). Anarea ratio of each peak in the gas chromatogram corresponds to the ratio(weight ratio) of the liquid crystal compound. When the capillarycolumns described above were used, a correction coefficient of each ofthe liquid crystal compounds may be regarded as 1 (one). Accordingly,the proportion (% by weight) of the liquid crystal compounds can becalculated from the area ratio of each peak.

Sample for measurement: When characteristics of the composition and thedevice were measured, the composition was used as a sample as was. Uponmeasuring characteristics of a compound, a sample for measurement wasprepared by mixing the compound (15% by weight) with a base liquidcrystal (85% by weight). Values of characteristics of the compound werecalculated, according to an extrapolation method, using values obtainedby measurement. (Extrapolated value)={(measured value of asample)−0.85×(measured value of a base liquid crystal)}/0.15. When asmectic phase (or crystals) precipitates at the ratio thereof at 25° C.,a ratio of the compound to the base liquid crystal was changed step bystep in the order of (10% by weight: 90% by weight), (5% by weight: 95%by weight) and (1% by weight: 99% by weight). Values of maximumtemperature, optical anisotropy, viscosity and dielectric anisotropywith regard to the compound were determined according to theextrapolation method.

A base liquid crystal described below was used. A proportion of thecomponent compound was expressed in terms of weight percent (% byweight).

Measuring method: Characteristics were measured according to the methodsdescribed below. Most of the measuring methods are applied as describedin the Standard of Japan Electronics and Information TechnologyIndustries Association (hereinafter abbreviated as JEITA) (JEITAED-2521B) discussed and established by JEITA, or modified thereon. Nothin film transistor (TFT) was attached to a TN device used formeasurement.

(1) Maximum temperature of nematic phase (NI; ° C.): A sample was placedon a hot plate in a melting point apparatus equipped with a polarizingmicroscope, and heated at a rate of 1° C. per minute. Temperature whenpart of the sample began to change from a nematic phase to an isotropicliquid was measured. A maximum temperature of the nematic phase may beoccasionally abbreviated as “maximum temperature.”

(2) Minimum temperature of nematic phase (T_(c); ° C.): Samples eachhaving a nematic phase were put in glass vials and kept in freezers attemperatures of 0° C., −10° C., −20° C., −30° C. and −40° C. for 10days, and then liquid crystal phases were observed. For example, whenthe sample was maintained in the nematic phase at −20° C. and changed tocrystals or a smectic phase at −30° C., T_(c) was expressed asT_(c)<−20° C. A minimum temperature of the nematic phase may beoccasionally abbreviated as “minimum temperature.”

(3) Viscosity (bulk viscosity; q; measured at 20° C.; mPa·s): Formeasurement, a cone-plate (E type) rotational viscometer made by TokyoKeiki Inc. was used.

(4) Viscosity (rotational viscosity; yl; measured at 25° C.; mPa·s):Measurement was carried out according to a method described in M. Imaiet al., Molecular Crystals and Liquid Crystals, Vol. 259, p. 37 (1995).A sample was put in a VA device in which a distance (cell gap) betweentwo glass substrates was 20 micrometers. Voltage was applied stepwise tothe device in the range from 39 V to 50 V at an increment of 1 V. Aftera period of 0.2 second with no voltage application, voltage wasrepeatedly applied under conditions of only one rectangular wave(rectangular pulse; 0.2 second) and no voltage application (2 seconds).A peak current and a peak time of transient current generated by theapplied voltage were measured. A value of rotational viscosity wasobtained from the measured values and calculation equation (8) describedon page 40 of the paper presented by M. Imai et al. Dielectricanisotropy required for the calculation was measured according tosection (6).

(5) Optical anisotropy (refractive index anisotropy; Δn; measured at 25°C.): Measurement was carried out by an Abbe refractometer with apolarizing plate mounted on an ocular, using light at a wavelength of589 nanometers. A surface of a main prism was rubbed in one direction,and then a sample was added dropwise onto the main prism. A refractiveindex (n∥) was measured when a direction of polarized light was parallelto a direction of rubbing. A refractive index (n⊥) was measured when thedirection of polarized light was perpendicular to the direction ofrubbing. A value of optical anisotropy was calculated from an equation:Δn=n∥−n⊥.

(6) Dielectric anisotropy (Δε; measured at 25° C.): A value ofdielectric anisotropy was calculated from an equation: Δε=ε∥−ε⊥. Adielectric constant (ε∥ and ε⊥) was measured as described below.

(1) Measurement of dielectric constant (ε∥): An ethanol (20 mL) solutionof octadecyltriethoxysilane (0.16 mL) was applied to a well-cleanedglass substrate. After rotating the glass substrate with a spinner, theglass substrate was heated at 150° C. for 1 hour. A sample was put in aVA device in which a distance (cell gap) between two glass substrateswas 4 micrometers, and the device was sealed with an ultraviolet-curableadhesive. Sine waves (0.5 V, 1 kHz) were applied to the device, andafter 2 seconds, a dielectric constant (ε∥) of liquid crystal moleculesin a major axis direction was measured.

(2) Measurement of dielectric constant (ε⊥): A polyimide solution wasapplied to a well-cleaned glass substrate. After calcining the glasssubstrate, rubbing treatment was applied to the alignment film obtained.A sample was put in a TN device in which a distance (cell gap) betweentwo glass substrates was 9 micrometers and a twist angle was 80 degrees.Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2seconds, a dielectric constant (ε⊥) of liquid crystal molecules in aminor axis direction was measured.

(7) Threshold voltage (Vth; measured at 25° C.; V): For measurement, anLCD-5100 luminance meter made by Otsuka Electronics Co., Ltd. was used.A light source was a halogen lamp. A sample was put in a normally blackmode VA device in which a distance (cell gap) between two glasssubstrates was 4 micrometers and a rubbing direction was anti-parallel,and the device was sealed with an ultraviolet-curable adhesive. Avoltage (60 Hz, rectangular waves) to be applied to the device wasstepwise increased from 0 V to 20 V at an increment of 0.02 V. On theoccasion, the device was irradiated with light from a directionperpendicular to the device, and an amount of light transmitted throughthe device was measured. A voltage-transmittance curve was prepared, inwhich the maximum amount of light corresponds to 100% transmittance andthe minimum amount of light corresponds to 0% transmittance. A thresholdvoltage is expressed in terms of voltage at 10% transmittance.

(8) Voltage holding ratio (VHR-1; measured at 25° C.; %): A TN deviceused for measurement had a polyimide alignment film, and a distance(cell gap) between two glass substrates was 5 micrometers. A sample wasput in the device, and then the device was sealed with anultraviolet-curable adhesive. A pulse voltage (60 microseconds at 5 V)was applied to the TN device and the device was charged. A decayingvoltage was measured for 16.7 milliseconds with a high-speed voltmeter,and area A between a voltage curve and a horizontal axis in a unit cyclewas determined. Area B is an area without decay. A voltage holding ratiois expressed in terms of a percentage of area A to area B.

(9) Voltage holding ratio (VHR-2; measured at 80° C.; %): A voltageholding ratio was measured according to procedures identical with theprocedures described above except that measurement was carried out at80° C. in place of 25° C. The thus obtained value was expressed in termsof VHR-2.

(10) Voltage holding ratio (VHR-3; measured at 25° C.; %): Stability toultraviolet light was evaluated by measuring a voltage holding ratioafter a device was irradiated with ultraviolet light. A TN device usedfor measurement had a polyimide alignment film and a cell gap was 5micrometers. A sample was injected into the device, and the device wasirradiated with light for 20 minutes. A light source was an ultrahigh-pressure mercury lamp USH-500D (made by Ushio, Inc.), and adistance between the device and the light source was 20 centimeters. Inmeasurement of VHR-3, a decaying voltage was measured for 16.7milliseconds. A composition having large VHR-3 has high stability toultraviolet light. A value of VHR-3 is preferably 90% or more, andfurther preferably 95% or more.

(11) Voltage holding ratio (VHR-4; measured at 25° C.; %): Stability toheat was evaluated by measuring a voltage holding ratio after a TNdevice into which a sample was injected was heated in aconstant-temperature bath at 80° C. for 500 hours. In measurement ofVHR-4, a decaying voltage was measured for 16.7 milliseconds. Acomposition having large VHR-4 has high stability to heat.

(12) Response time (τ; measured at 25° C.; ms): For measurement, anLCD-5100 luminance meter made by Otsuka Electronics Co., Ltd. was used.A light source was a halogen lamp. A low-pass filter was set to 5 kHz. Asample was put in a normally black mode VA device in which a distance(cell gap) between two glass substrates was 4 micrometers and a rubbingdirection was anti-parallel. The device was sealed with anultraviolet-curable adhesive. A voltage (rectangular waves; 60 Hz, 10 V,0.5 second) was applied to the device. On the occasion, the device wasirradiated with light from a direction perpendicular to the device, andan amount of light transmitted through the device was measured. Themaximum amount of light corresponds to 100% transmittance, and theminimum amount of light corresponds to 0% transmittance. A response timewas expressed in terms of time required for a change from 90%transmittance to 10% transmittance (fall time; millisecond).

(13) Specific resistance (ρ; measured at 25° C.; Ω cm): Into a vesselequipped with electrodes, 1.0 milliliter of sample was injected. Adirect current voltage (10 V) was applied to the vessel, and a directcurrent after 10 seconds was measured. Specific resistance wascalculated from the following equation: (specificresistance)={(voltage)×(electric capacity of a vessel)}/{(directcurrent)×(dielectric constant of vacuum)}.

Examples of compositions were described below. The component compoundswere represented using symbols according to definitions in Table 3described below. In Table 3, the configuration of 1,4-cyclohexylene istrans. A parenthesized number next to a symbolized compound represents achemical formula to which the compound belongs. A symbol (−) means anyother liquid crystal compound. A proportion (percentage) of the liquidcrystal compound is expressed in terms of weight percent (% by weight)based on the weight of the liquid crystal composition containing noadditive. Values of the characteristics of the composition weresummarized in a last part.

TABLE 3 Method for description of compounds using symbols R—(A₁)—Z₁— . .. —Z_(n)—(A_(n))—R′ 1) Left-terminal group R— Symbol F—C_(n)H_(2n)— Fn-C_(n)H_(2n+1)— n- C_(n)H_(2n+1)O— nO- C_(m)H_(2m+1)OC_(n)H_(2n)— mOn-CH₂═CH— V- C_(n)H_(2n+1)—CH═CH— nV- CH₂═CH—C_(n)H_(2n)— Vn-C_(m)H_(2m+1)—CH═CH—C_(n)H_(2n)— mVn- CF₂═CH— VFF- CF₂═CH—C_(n)H_(2n)—VFFn- CH₂═CH—COO— AC- CH₂═C(CH₃)—COO— MAC- 2) Right-terminal group —R′Symbol —C_(n)H_(2n+1) -n —OC_(n)H_(2n+1) -On —CH═CH₂ -V—CH═CH—C_(n)H_(2n+1) -Vn —C_(n)H_(2n)—CH═CH₂ -nV—C_(m)H_(2m)—CH═CH—C_(n)H_(2n+1) -mVn —CH═CF₂ -VFF —OCO—CH═CH₂ -AC—OCO—C(CH₃)═CH₂ -MAC 3) Bonding group —Z_(n)— Symbol —C_(n)H_(2n)— n—COO— E —CH═CH— V —CH═CHO— VO —OCH═CH— OV —CH₂O— 1O —OCH₂— O1 4) Ringstructure —A_(n)— Symbol

H

B

B(F)

B(2F)

B(F,F)

B(2F,5F)

B(2F,3F)

B(2F,3Cl)

dh

Dh

ch

Cro(7F,8F) 5) Examples of description Example 1 4O-B(2F,3F)2BB(2F,3F)-O2

Example 2 3-HH-V

Example 3 V-HHB-1

Example 4 3-HHB(2F,3F)-O2

Comparative Example 1

From compositions disclosed in WO 2009/125668 A1, Example 15 wasselected. The basis is that the composition contains compound (1-7) andcompound (1-8) being a first component.

2O—B(2F,3F)O1HB(2F,3F)—O2 (1-7)  5% 2O—B(2F,3F)O1BB(2F,3F)—O2 (1-8)  5%3-HB(2F,3F)—O2 (3-1) 12% 5-HB(2F,3F)—O2 (3-1) 12% 3-HHB(2F,3F)—O2 (3-6) 8% 5-HHB(2F,3F)—O2 (3-6)  9% 3-HB—O2 (4-1) 14% 5-HB—O2 (4-1) 15%3-HHB-1 (4-4) 10% 3-HHB-3 (4-4) 10%

NI=82.3° C.; Tc<−20° C.; η=25.4 mPa·s; Δn=0.099; Δε=−3.3.

Example 1

2O—B(2F,3F)O1HB(2F,3F)—O2 (1-7)  5% 2O—B(2F,3F)O1BB(2F,3F)—O2 (1-8)  5%3-HH—V (2-14) 29% 3-HB(2F,3F)—O2 (3-1) 12% 5-HB(2F,3F)—O2 (3-1) 12%3-HHB(2F,3F)—O2 (3-6)  8% 5-HHB(2F,3F)—O2 (3-6)  9% 3-HHB-1 (4-4) 10%3-HHB-3 (4-4) 10%

NI=84.8° C.; Tc<−20° C.; η=19.1 mPa·s; Δn=0.068; Δε=−2.9.

Example 2

2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  3% 4O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  4%3-HH—V (2-14) 32% V—HB(2F,3F)—O2 (3-1)  6% 3-BB(2F,3F)—O2 (3-4)  7%V2—BB(2F,3F)—O2 (3-4)  8% 2-HHB(2F,3F)—O2 (3-6)  3% 3-HHB(2F,3F)—O2(3-6)  8% V—HHB(2F,3F)—O2 (3-6) 10% V—HHB(2F,3F)—O4 (3-6)  6%3-HBB(2F,3F)—O2 (3-10)  7% 3-DhB(F)B(2F,3F)—O2 (3)  4% V—HHB-1 (4-4)  2%

NI=75.3° C.; Tc<−20° C.; η=15.3 mPa·s; Δn=0.106; Δε=−4.2.

Example 3

2O—B(2F,3F)2HB(2F,3F)—O2 (1-3)  3% 2O—B(2F,3F)O1BB(2F,3F)—O2 (1-8)  4%3-HH—V (2-14) 33% 3-H2B(2F,3F)—O2 (3-2)  3% 3-BB(2F,3F)—O2 (3-4)  5%5-BB(2F,3F)—O2 (3-4)  4% 3-HHB(2F,3F)—O2 (3-6)  5% V—HHB(2F,3F)—O2 (3-6) 5% 3-HH2B(2F,3F)—O2 (3-7)  3% 5-HH2B(2F,3F)—O2 (3-7)  3%V—HH1OB(2F,3F)—O2 (3-8)  3% 2-HBB(2F,3F)—O2 (3-10)  5% 3-HHB(2F,3Cl)—O2(3-12)  2% 5-HHB(2F,3Cl)—O2 (3-12)  3% 3-HchB(2F,3F)—O2 (3-19)  2%3-BB(2F)B(2F,3F)—O2 (3-20)  4% 3-BB(F)B(2F,3F)—O2 (3-21)  2%3-dhB(F)B(2F,3F)—O2 (3)  3% 5-HB—O2 (4-1)  2% V2—BB-1 (4-2)  2% 3-HBB-2(4-5)  4%

NI=82.6° C.; Tc<−20° C.; η=14.3 mPa·s; Δn=0.111; Δε=−3.7.

Example 4

2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  4% 4O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  6%3-HH—V (2-14) 29% 3-HH—V1 (2-15) 11% 3-HH—VFF (2-18)  5% V—HB(2F,3F)—O2(3-1)  3% 3-H1OB(2F,3F)—O2 (3-3)  3% 3-B(2F,3F)B(2F,3F)—O2 (3-5)  3%3-HHB(2F,3F)—O2 (3-6)  8% 4-HHB(2F,3F)—O2 (3-6)  4% 3-HH1OB(2F,3F)—O2(3-8)  4% 2-BB(2F,3F)B-3 (3-9)  3% 3-HBB(2F,3Cl)—O2 (3-13)  2%5-HBB(2F,3Cl)—O2 (3-13)  2% 3-HH1OCro(7F,8F)-5 (3-15)  2%3-B(2F)B(2F,3F)—O2 (3-22)  2% 3-DhB(F)B(2F,3F)—O2 (3)  3% V2—HHB-1 (4-4) 2% 1-BB(F)B—2V (4-6)  2% V2—BB2B-1 (4-8)  2%

NI=76.9° C.; Tc<−20° C.; η=12.1 mPa·s; Δn=0.102; Δε=−3.5.

Example 5

2O—B(2F,3F)2HB(2F,3F)—O2 (1-3)  2% 2O—B(2F,3F)O1HB(2F,3F)—O2 (1-7)  2%4O—B(2F,3F)O1BB(2F,3F)—O2 (1-8)  2% 3-HH—V (2-14) 28% 3-HB(2F,3F)—O2(3-1)  4% 5-HB(2F,3F)—O2 (3-1)  5% 2-HHB(2F,3F)—O2 (3-6)  3%3-HHB(2F,3F)—O2 (3-6)  3% 2-HBB(2F,3F)—O2 (3-10)  6% 3-HBB(2F,3F)—O2(3-10)  8% 3-HEB(2F,3F)B(2F,3F)—O2 (3-11)  3% 3-H1OCro(7F,8F)-5 (3-14) 2% 3-chB(2F,3F)—O2 (3-18)  3% V—chB(2F,3F)—O2 (3-18)  3%3-DhB(2F)B(2F,3F)—O2 (3)  4% 3-HHEH-3 (4-3)  3% 5-B(F)BB-3 (4-7)  3%5-HB(F)BH-3 (4-11)  3% 2-HH-3 (—) 10% 1O1—HBBH-5 (—)  3%

NI=80.1° C.; Tc<−20° C.; η=15.8 mPa·s; Δn=0.103; Δε=−3.4.

Example 6

2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  3% 4O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  4%2O—B(2F,3F)O1HB(2F,3F)—O2 (1-7)  3% 3-HH—V (2-14) 24% 3-HH—V1 (2-15)  5%3-HB(2F,3F)—O2 (3-1)  3% 3-BB(2F,3F)—O2 (3-4)  3% 5-BB(2F,3F)—O2 (3-4) 3% 2-HHB(2F,3F)—O2 (3-6)  4% 3-HHB(2F,3F)—O2 (3-6)  8% V—HHB(2F,3F)—O2(3-6)  3% V—HH1OB(2F,3F)—O2 (3-8)  3% 2-HBB(2F,3F)—O2 (3-10)  5%3-HBB(2F,3F)—O2 (3-10)  8% 3-DhB(F)B(2F,3F)—O2 (3)  3% 1-BB-3 (4-2)  3%1-BB-5 (4-2)  3% 3-HHB-1 (4-4)  3% 3-HHEBH-3 (4-10)  4% 2-HH-3 (—)  5%

NI=88.2° C.; Tc<−20° C.; η=14.7 mPa·s; Δn=0.110; Δε=—3.7.

Example 7

2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  3% 4O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  2%3-HH—V (2-14) 29% 3-HH—V1 (2-15)  6% 3-HB(2F,3F)—O2 (3-1)  5%3-BB(2F,3F)—O2 (3-4)  5% 2-HHB(2F,3F)—O2 (3-6)  5% 3-HHB(2F,3F)—O2 (3-6) 7% 2-HBB(2F,3F)—O2 (3-10)  5% 3-HBB(2F,3F)—O2 (3-10) 10%5-BB(2F)B(2F,3F)—O2 (3-20)  2% 3-BB(F)B(2F,3F)—O2 (3-21)  2%3-DhB(2F)B(2F,3F)—O2 (3)  5% 3-HB—O2 (4-1)  3% 3-HB(F)HH-2 (4-9)  3%3-HBB(F)B-2 (4-12)  3% 2-HH-3 (—)  5%

NI=86.2° C.; Tc<−20° C.; η=13.9 mPa·s; Δn=0.111; Δε=−3.3.

Example 8

2O—B(2F,3F)2HB(2F,3F)—O2 (1-3)  2% 2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  2%4O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  2% 6O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  2%2O—B(2F,3F)O1HB(2F,3F)—O2 (1-7)  2% 2O—B(2F,3F)O1BB(2F,3F)—O2 (1-8)  2%3-HH—V (2-14) 29% V—HB(2F,3F)—O2 (3-1)  3% 5-HB(2F,3F)—O2 (3-1)  2%5-H2B(2F,3F)—O2 (3-2)  2% 2-H1OB(2F,3F)—O2 (3-3)  3% 3-HHB(2F,3F)—O2(3-6)  7% 4-HHB(2F,3F)—O2 (3-6)  2% 2-HH1OB(2F,3F)—O2 (3-8)  3%3-HBB(2F,3F)—O2 (3-10)  8% 3-HH1OCro(7F,8F)-5 (3-15)  3%3-HchB(2F,3F)—O2 (3-19)  3% 3-DhB(F)B(2F,3F)—O2 (3)  3% V—HBB-3 (4-5) 5% 2-BB(F)B—2V (4-6)  3% 3-BB(F)B—2V (4-6)  3% 2-HH-3 (—)  9%

NI=81.5° C.; Tc<−20° C.; η=16.0 mPa·s; Δn=0.106; Δε=−3.7.

Example 9

2O—B(2F,3F)O1HB(2F,3F)—O2 (1-7) 3% 2O—B(2F,3F)O1BB(2F,3F)—O2 (1-8) 3%3-HH—V (2-14) 33% V—HB(2F,3F)—O2 (3-1) 5% 3-HB(2F,3F)—O2 (3-1) 7%3-HHB(2F,3F)—O2 (3-6) 6% 4-HHB(2F,3F)—O2 (3-6) 3% V—HHB(2F,3F)—O2 (3-6)3% 3-HBB(2F,3F)—O2 (3-10) 6% 5-HBB(2F,3F)—O2 (3-10) 7% 3-H1OCro(7F,8F)-5(3-14) 2% 3-HDhB(2F,3F)—O2 (3-16) 3% 3-dhBB(2F,3F)—O2 (3-17) 2%5-HchB(2F,3F)—O2 (3-19) 3% 3-dhB(F)B(2F,3F)—O2 (3) 3% 3-HBB-2 (4-5) 8%F3—HH—V (—) 3%

NI=84.8° C.; Tc<−20° C.; η=15.0 mPa·s; Δn=0.101; Δε=−3.7.

Example 10

2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  3% 6O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  4%3-HH—V (2-14) 20% 3-HH—V1 (2-15)  8% 5-HH—V (2)  3% 5-HB(2F,3F)—O2 (3-1) 4% 3-H1OB(2F,3F)—O2 (3-3)  3% 3-BB(2F,3F)—O2 (3-4)  8% 2O—BB(2F,3F)—O2(3-4)  5% 4-HHB(2F,3F)—O2 (3-6)  4% V—HHB(2F,3F)—O2 (3-6) 10%3-HBB(2F,3F)—O2 (3-10)  5% 4-HBB(2F,3F)—O2 (3-10)  5%3-DhB(F)B(2F,3F)—O4 (3)  3% 1V2—BB-1 (4-2)  3% 3-HHEBH-4 (4-10)  3%5-HBB(F)B-3 (4-12)  3% 2-HH-5 (—)  3% 3-HH-4 (—)  3%

NI=84.6° C.; Tc<−20° C.; η=13.7 mPa·s; Δn=0.112; Δε=−3.7.

Example 11

4O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  5% 6O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  5%3-HH—V (2-14) 32% 3-HB(2F,3F)—O2 (3-1) 10% 3-H2B(2F,3F)—O2 (3-2)  4%2O—BB(2F,3F)—O2 (3-4)  5% 3-HHB(2F,3F)—O2 (3-6) 12% 2-BB(2F,3F)B-3 (3-9) 3% 2-BB(2F,3F)B-4 (3-9)  3% V—HBB(2F,3F)—O2 (3-10)  5%3-HEB(2F,3F)B(2F,3F)—O2 (3-11)  2% V2—HchB(2F,3F)—O2 (3-19)  3%5-DhB(2F)B(2F,3F)—O2 (3)  3% 5-B(F)BB-2 (4-7)  2% 3-HHEBH-5 (4-10)  3%5-HH—O1 (—)  3%

NI=80.3° C.; Tc<−20° C.; η=15.0 mPa·s; Δn=0.112; Δε=−3.7.

Example 12

2O—B(2F,3F)2HB(2F,3F)—O2 (1-3)  3% 2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  3%4O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  3% 2O—B(2F,3F)O1BB(2F,3F)—O2 (1-8)  2%3-HH—V (2-14) 23% 5-HB(2F,3F)—O2 (3-1)  2% 3-BB(2F,3F)—O2 (3-4)  5%2-HHB(2F,3F)—O2 (3-6)  4% V—HHB(2F,3F)—O2 (3-6)  4% V—HHB(2F,3F)—O4(3-6)  5% 3-HBB(2F,3F)—O2 (3-10) 10% 5-HBB(2F,3F)—O2 (3-10)  5%3-DhB(2F)B(2F,3F)—O2 (3)  3% 7-HB-1 (4-1)  3% 1-BB-3 (4-2)  3% 3-HHEH-5(4-3)  3% 3-HHB-3 (4-4)  3% V2—HHB-1 (4-4)  3% 2-BB(F)B-3 (4-6)  3%2-HH-3 (—) 10%

NI=84.2° C.; Tc<−20° C.; η=14.3 mPa·s; Δn=0.110; Δε=−3.4.

Example 13

2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  3% 4O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  4%6O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  5% 3-HH—V (2-14) 32% 3-HH—V1 (2-15)  9%3-HB(2F,3F)—O2 (3-1)  8% 2O—BB(2F,3F)—O2 (3-4)  3% 3-HHB(2F,3F)—O2 (3-6) 6%. 3-HBB(2F,3F)—O2 (3-10)  6% V—HBB(2F,3F)—O2 (3-10)  5%3-H1OCro(7F,8F)-5 (3-14)  2% 3-HH1OCro(7F,8F)-5 (3-15)  2%3-DhB(F)B(2F,3F)—O1 (3)  3% 3-HHB—O1 (4-4)  3% VFF—HHB-1 (4-4)  3%V—HBB-3 (4-5)  3% 2-BB(F)B-5 (4-6)  3%

NI=81.8° C.; Tc<−20° C.; η=13.3 mPa·s; Δn=0.109; Δε=−3.4.

Example 14

2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  3% 6O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  4%2O—B(2F,3F)O1HB(2F,3F)—O2 (1-7)  3% 3-HH—V (2-14) 29% 2-H1OB(2F,3F)—O2(3-3)  2% 3-H1OB(2F,3F)—O2 (3-3)  2% 3-BB(2F,3F)—O2 (3-4)  2%2-HHB(2F,3F)—O2 (3-6)  3% 3-HHB(2F,3F)—O2 (3-6)  3% 4-HHB(2F,3F)—O2(3-6)  4% 2-BB(2F,3F)B-3 (3-9)  3% 2-HBB(2F,3F)—O2 (3-10)  7%3-HBB(2F,3F)—O2 (3-10)  7% 5-HBB(2F,3F)—O2 (3-10)  8% 3-chB(2F,3F)—O2(3-18)  3% 3-dhB(F)B(2F,3F)—O2 (3)  3% 3-HB—O2 (4-1)  2% V—HBB-2 (4-5) 3% 2-HH-3 (—)  9%

NI=81.6° C.; Tc<−20° C.; η=14.5 mPa·s; Δn=0.111; Δε=−3.8.

Example 15

2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  4% 4O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  5%6O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  6% 3-HH—V (2-14) 25% 3-HH—V1 (2-15)  9%3-HB(2F,3F)—O2 (3-1)  9% 5-HB(2F,3F)—O2 (3-1)  5% 5-BB(2F,3F)—O2 (3-4) 2% 3-HHB(2F,3F)—O2 (3-6)  4% V—HHB(2F,3F)—O2 (3-6)  7% 3-HBB(2F,3F)—O2(3-10)  3% 4-HBB(2F,3F)—O2 (3-10)  3% V—HBB(2F,3F)—O2 (3-10)  3%3-DhB(2F)B(2F,3F)—O1 (3)  3% 1-BB-3 (4-2)  3% 3-HHB-1 (4-4)  3%VFF2—HHB-1 (4-4)  3% 3-HH—O1 (—)  3%

NI=74.9° C.; Tc<−20° C.; η=13.7 mPa·s; Δn=0.105; Δε=−3.9.

Example 16

2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  4% 1V2—HH—2V1 (2-10)  5% 3-HH—V (2-14)30% V—HB(2F,3F)—O2 (3-1)  5% 3-H2B(2F,3F)—O2 (3-2)  4% 2-HHB(2F,3F)—O2(3-6)  5% 4-HHB(2F,3F)—O2 (3-6)  6% 2-HH1OB(2F,3F)—O2 (3-8)  3%3-HH1OB(2F,3F)—O2 (3-8)  3% 2-BB(2F,3F)B-3 (3-9)  3% 3-HBB(2F,3F)—O2(3-10)  7% 5-HBB(2F,3F)—O2 (3-10)  8% V2—HchB(2F,3F)—O2 (3-19)  4%3-dhB(F)B(2F,3F)—O2 (3)  4% 3-HB—O2 (4-1)  6% 5-HB—O2 (4-1)  3%

NI=84.3° C.; Tc<−20° C.; η=12.5 mPa·s; Δn=0.104; Δε=−3.6.

Example 17

2O—B(2F,3F)O1HB(2F,3F)—O2 (1-7)  5% 2O—B(2F,3F)O1BB(2F,3F)—O2 (1-8)  5%V—HH—V (2-1) 15% 3-HH—V (2-14) 14% 3-HB(2F,3F)—O2 (3-1) 12%5-HB(2F,3F)—O2 (3-1) 12% 3-HHB(2F,3F)—O2 (3-6)  8% 5-HHB(2F,3F)—O2 (3-6) 9% 3-HHB-1 (4-4) 10% 3-HHB-3 (4-4) 10%

NI=79.6° C.; Tc<−20° C.; η=17.7 mPa·s; Δn=0.048; Δε=−2.9.

Example 18

2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  3% 4O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  4%V—HH—V (2-1)  5% 1V—HH—V1 (2-5)  5% 3-HH—V (2-14) 22% V—RB(2F,3F)—O2(3-1)  6% 3-BB(2F,3F)—O2 (3-4)  7% V2—BB(2F,3F)—O2 (3-4)  8%2-HHB(2F,3F)—O2 (3-6)  3% 3-HHB(2F,3F)—O2 (3-6)  8% V—HHB(2F,3F)—O2(3-6) 10% V—HHB(2F,3F)—O4 (3-6)  6% 3-HBB(2F,3F)—O2 (3-10)  7%3-DhB(F)B(2F,3F)—O2 (3)  4% V—HHB-1 (4-4)  2%

NI=78.0° C.; Tc<−20° C.; η=14.6 mPa·s; Δn=0.110; Δε=−4.2.

Example 19

2O—B(2F,3F)2HB(2F,3F)—O2 (1-3)  3% 2O—B(2F,3F)O1BB(2F,3F)—O2 (1-8)  4%V—HH—V1 (2-2) 10% V—HH—2V1 (2-4)  5% 3-HH—V (2-14) 18% 3-H2B(2F,3F)—O2(3-2)  3% 3-BB(2F,3F)—O2 (3-4)  5% 5-BB(2F,3F)—O2 (3-4)  4%3-HHB(2F,3F)—O2 (3-6)  5% V—HHB(2F,3F)—O2 (3-6)  5% 3-HH2B(2F,3F)—O2(3-7)  3% 5-HH2B(2F,3F)—O2 (3-7)  3% V—HH1OB(2F,3F)—O2 (3-8)  3%2-HBB(2F,3F)—O2 (3-10)  5% 3-HHB(2F,3C1)—O2 (3-12)  2% 5-HHB(2F,3C1)—O2(3-12)  3% 3-HchB(2F,3F)—O2 (3-19)  2% 3-BB(2F)B(2F,3F)—O2 (3-20)  4%3-BB(F)B(2F,3F)—O2 (3-21)  2% 3-dhB(F)B(2F,3F)—O2 (3)  3% 5-HB—O2 (4-1) 2% V2—BB-1 (4-2)  2% 3-HBB-2 (4-5)  4%

NI=87.2° C.; Tc<−20° C.; η=13.9 mPa·s; Δn=0.117; Δε=−3.7.

Example 20

2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  3% 4O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  4%2O—B(2F,3F)O1HB(2F,3F)—O2 (1-7)  3% V—HH—V (2-1)  5% 1V—HH—V1 (2-5)  5%3-HH—V (2-14) 14% 3-HH—V1 (2-15)  5% 3-HB(2F,3F)—O2 (3-1)  3%3-BB(2F,3F)—O2 (3-4)  3% 5-BB(2F,3F)—O2 (3-4)  3% 2-HHB(2F,3F)—O2 (3-6) 4% 3-HHB(2F,3F)—O2 (3-6)  8% V—HHB(2F,3F)—O2 (3-6)  3%V—HH1OB(2F,3F)—O2 (3-8)  3% 2-HBB(2F,3F)—O2 (3-10)  5% 3-HBB(2F,3F)—O2(3-10)  8% 3-DhB(F)B(2F,3F)—O2 (3)  3% 1-BB-3 (4-2)  3% 1-BB-5 (4-2)  3%3-HHB-1 (4-4)  3% 3-HHEBH-3 (4-10)  4% 2-HH-3 (—)  5%

NI=90.9° C.; Tc<−20° C.; η=14.1 mPa·s; Δn=0.113; Δε=−3.7.

Example 21

2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  3% 6O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  4%V—HH—V (2-1) 10% 3-HH—V (2-14) 15% 3-HH—V1 (2-15)  3% 5-HH—V (2)  3%5-HB(2F,3F)—O2 (3-1)  4% 3-H1OB(2F,3F)—O2 (3-3)  3% 3-BB(2F,3F)—O2 (3-4) 8% 2O—BB(2F,3F)—O2 (3-4)  5% 4-HHB(2F,3F)—O2 (3-6)  4% V—HHB(2F,3F)—O2(3-6) 10% 3-HBB(2F,3F)—O2 (3-10)  5% 4-HBB(2F,3F)—O2 (3-10)  5%3-DhB(F)B(2F,3F)—O4 (3)  3% 1V2—BB-1 (4-2)  3% 3-HHEBH-4 (4-10)  3%5-HBB(F)B-3 (4-12)  3% 2-HH-5 (—)  3% 3-HH-4 (—)  3%

NI=83.8° C.; Tc<−20° C.; η=12.4 mPa·s; Δn=0.113; Δε=−3.7.

Example 22

2O—B(2F,3F)2HB(2F,3F)—O2 (1-3)  3% 2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  3%4O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  3% 2O—B(2F,3F)O1BB(2F,3F)—O2 (1-8)  2%V—HH—V (2-1) 10% V—HH—2V1 (2-4)  3% 1V2—HH—2V1 (2-10)  5% 3-HH—V (2-14)10% 5-HB(2F,3F)—O2 (3-1)  2% 3-BB(2F,3F)—O2 (3-4)  5% 2-HHB(2F,3F)—O2(3-6)  4% V—HHB(2F,3F)—O2 (3-6)  4% V—HHB(2F,3F)—O4 (3-6)  5%3-HBB(2F,3F)—O2 (3-10) 10% 5-HBB(2F,3F)—O2 (3-10)  5%3-DhB(2F)B(2F,3F)—O2 (3)  3% 7-HB-1 (4-1)  3% 1-BB-3 (4-2)  3% 3-HHEH-5(4-3)  3% 3-HHB-3 (4-4)  3% V2—HHB-1 (4-4)  3% 2-BB(F)B-3 (4-6)  3%2-HH-3 (—)  5%

NI=89.0° C.; Tc<−20° C.; η=13.0 mPa·s; Δn=0.116; Δε=−3.4.

Example 23

2O—B(2F,3F)2BB(2F,3F)—O2 (1-6)  4% V—HH—V1 (2-2)  3% 1V2—HH—2V1 (2-10)10% VFF—HH—VFF (2-13)  2% 3-HH—V (2-14) 20% V—HB(2F,3F)—O2 (3-1)  5%3-H2B(2F,3F)—O2 (3-2)  4% 2-HHB(2F,3F)—O2 (3-6)  5% 4-HHB(2F,3F)—O2(3-6)  6% 2-HH1OB(2F,3F)—O2 (3-8)  3% 3-HH1OB(2F,3F)—O2 (3-8)  3%2-BB(2F,3F)B-3 (3-9)  3% 3-HBB(2F,3F)—O2 (3-10)  7% 5-HBB(2F,3F)—O2(3-10)  8% V2—HchB(2F,3F)—O2 (3-19)  4% 3-dhB(F)B(2F,3F)—O2 (3)  4%3-HB—O2 (4-1)  6% 5-HB—O2 (4-1)  3%

NI=88.7° C.; η=12.9 mPa·s; Δn=0.109; Δε=−3.7.

The viscosity of the composition in Comparative Example 1 was 25.4mPa·s. On the other hand, the viscosity of the compositions in Examples1 to 23 were from 12.1 mPa·s to 19.1 mPa·s. Thus, the composition inExamples each has lower viscosity in comparison with the composition inComparative Examples. Accordingly, the liquid crystal composition of theinvention is concluded to have superb characteristics.

INDUSTRIAL APPLICABILITY

A liquid crystal composition of the invention can be used in a liquidcrystal monitor, a liquid crystal television and so forth.

What is claimed is:
 1. A liquid crystal composition that has negativedielectric anisotropy, and contains at least one compound selected fromcompounds represented by formula (1) and at least one compound selectedfrom compounds represented by formula (2):

wherein, in formula (1) and formula (2), R¹ and R² are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, or alkylhaving 1 to 12 carbons in which at least one hydrogen is replaced byfluorine or chlorine; R³ is alkyl having 1 to 12 carbons, alkenyl having2 to 12 carbons, or alkenyl having 2 to 12 carbons in which at least onehydrogen is replaced by fluorine or chlorine; R⁴ is alkenyl having 2 to12 carbons, or alkenyl having 2 to 12 carbons in which at least onehydrogen is replaced by fluorine or chlorine; ring A is1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene,2,3-difluoro-1,4-phenylene, tetrahydropyran-2,5-diyl,pyrimidine-2,5-diyl or pyridine-2,5-diyl; L¹, L², L³ and L⁴ areindependently hydrogen or fluorine, in which at least three thereof isfluorine; and Z¹ is a single bond, ethylene, carbonyloxy ormethyleneoxy.
 2. The liquid crystal composition according to claim 1,containing at least one compound selected from the group of compoundsrepresented by formula (1-1) to formula (1-8) as the at least onecompound selected from compounds represented by formula (1):

wherein, in formula (1-1) to formula (1-8), R¹ and R² are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, or alkylhaving 1 to 12 carbons in which at least one hydrogen is replaced byfluorine or chlorine.
 3. The liquid crystal composition according toclaim 1, containing at least one compound selected from the group ofcompounds represented by formula (2-1) to formula (2-18) as the at leastone compound selected from compounds represented by formula (2):


4. The liquid crystal composition according to claim 1, wherein aproportion of the at least one compound selected from compoundsrepresented by formula (1) is in the range from 3% by weight to 25% byweight, and a proportion of the at least one compound selected fromcompounds represented by formula (2) is in the range from 15% by weightto 70% by weight.
 5. The liquid crystal composition according to claim1, containing at least one compound selected from compounds representedby formula (3):

wherein, in formula (3), R⁵ and R⁶ are independently alkyl having 1 to12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkenyloxy having 2 to 12 carbons, or alkyl having 1 to 12carbons in which at least one hydrogen is replaced by fluorine orchlorine; ring B and ring D are independently 1,4-cyclohexylene,1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl,1,4-phenylene in which at least one hydrogen is replaced by fluorine orchlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl in which at leastone hydrogen is replaced by fluorine or chlorine, chroman-2,6-diyl, orchroman-2,6-diyl in which at least one hydrogen is replaced by fluorineor chlorine; ring C is 2,3-difluoro-1,4-phenylene,2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene,3,4,5-trifluoronaphthalene-2,6-diyl or 7,8-difluorochroman-2,6-diyl; Z²and Z³ are independently a single bond, ethylene, carbonyloxy ormethyleneoxy; and a is 1, 2 or 3, b is 0 or 1, and a sum of a and b is 3or less; however, compounds represented by formula (1) are excluded fromcompounds represented by formula (3):

wherein, in formula (1), R¹ and R² are independently alkyl having 1 to12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkenyloxy having 2 to 12 carbons, or alkyl having 1 to 12carbons in which at least one hydrogen is replaced by fluorine orchlorine; ring A is 1,4-cyclohexylene, 1,4-phenylene,2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene,tetrahydropyran-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl; L¹,L², L³ and L⁴ are independently hydrogen or fluorine, in which at leastthree thereof is fluorine; and Z¹ is a single bond, ethylene,carbonyloxy or methyleneoxy.
 6. The liquid crystal composition accordingto claim 5, containing at least one compound selected from the group ofcompounds represented by formula (3-1) to formula (3-22) as the at leastone compound selected from compounds represented by formula (3):

wherein, in formula (3-1) to formula (3-22), R⁵ and R⁶ are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, or alkylhaving 1 to 12 carbons in which at least one hydrogen is replaced byfluorine or chlorine.
 7. The liquid crystal composition according toclaim 5, wherein a proportion of the at least one compound selected fromcompounds represented by formula (3) is in the range from 20% by weightto 75% by weight.
 8. The liquid crystal composition according to claim1, containing at least one compound selected from compounds representedby formula (4):

wherein, in formula (4), R⁷ and R⁸ are independently alkyl having 1 to12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkyl having 1 to 12 carbons in which at least one hydrogen isreplaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons inwhich at least one hydrogen is replaced by fluorine or chlorine; ring Eand ring F are independently 1,4-cyclohexylene, 1,4-phenylene,2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; Z⁴ is a singlebond, ethylene or carbonyloxy; c is 1, 2 or 3; and ring F is1,4-phenylene when c is
 1. 9. The liquid crystal composition accordingto claim 8, containing at least one compound selected from the group ofcompounds represented by formula (4-1) to formula (4-12) as the at leastone compound selected from compounds represented by formula (4):

wherein, in formula (4-1) to formula (4-12), R⁷ and R⁸ are independentlyalkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenylhaving 2 to 12 carbons, alkyl having 1 to 12 carbons in which at leastone hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to12 carbons in which at least one hydrogen is replaced by fluorine orchlorine.
 10. The liquid crystal composition according to claim 8,wherein a proportion of the at least one compound selected fromcompounds represented by formula (4) is in the range from 2% by weightto 30% by weight.
 11. The liquid crystal composition according to claim5, containing at least one compound selected from compounds representedby formula (4):

wherein, in formula (4), R⁷ and R⁸ are independently alkyl having 1 to12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12carbons, alkyl having 1 to 12 carbons in which at least one hydrogen isreplaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons inwhich at least one hydrogen is replaced by fluorine or chlorine; ring Eand ring F are independently 1,4-cyclohexylene, 1,4-phenylene,2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; Z⁴ is a singlebond, ethylene or carbonyloxy; c is 1, 2 or 3; and ring F is1,4-phenylene when c is
 1. 12. The liquid crystal composition accordingto claim 1, containing at least one compound selected from polymerizablecompounds represented by formula (5) as an additive:

wherein, in formula (5), ring G and ring J are independently cyclohexyl,cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl,1,3-dioxane-2-yl, pyrimidine-2-yl or pyridine-2-yl, and in these rings,at least one hydrogen may be replaced by fluorine, chlorine, alkylhaving 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1to 12 carbons in which at least one hydrogen is replaced by fluorine orchlorine; ring I is 1,4-cyclohexylene, 1,4-cyclohexenylene,1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl,naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl,naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl,naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl,1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, and inthese rings, at least one hydrogen may be replaced by fluorine,chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons,or alkyl having 1 to 12 carbons in which at least one hydrogen isreplaced by fluorine or chlorine; Z⁵ and Z⁶ are independently a singlebond or an alkylene having 1 to 10 carbons, and in the alkylene, atleast one piece of —CH₂— may be replaced by —O—, —CO—, —COO— or —OCO—,and at least one piece of —CH₂—CH₂— may be replaced by —CH═CH—,—C(CH₃)═CH—, —CH═C(CH₃)— or —C(CH₃)═C(CH₃)—, and in these groups, atleast one hydrogen may be replaced by fluorine or chlorine; P¹, P² andP³ are independently a polymerizable group; Sp¹, Sp² and Sp³ areindependently a single bond or alkylene having 1 to 10 carbons, and inthe alkylene, at least one piece of —CH₂— may be replaced by —O—, —COO—,—OCO— or —OCOO—, and at least one piece of —CH₂—CH₂— may be replaced by—CH═CH— or and in these groups, at least one hydrogen may be replaced byfluorine or chlorine; d is 0, 1 or 2; and e, f and g are independently0, 1, 2, 3 or 4, and a sum of e, f and g is 1 or more.
 13. The liquidcrystal composition according to claim 12, wherein, in formula (5), P¹,P² and P³ are independently a group selected from the group ofpolymerizable groups represented by formula (P-1) to formula (P-5):

wherein, in formula (P-1) to formula (P-5), M¹, M² and M³ areindependently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkylhaving 1 to 5 carbons in which at least one hydrogen is replaced byfluorine or chlorine.
 14. The liquid crystal composition according toclaim 12, containing at least one compound selected from the group ofpolymerizable compounds represented by formula (5-1) to formula (5-27)as the additive:

wherein, in formula (5-1) to formula (5-27), P′, P² and P³ areindependently a group selected from the group of polymerizable groupsrepresented by formula (P-1) to formula (P-3):

wherein M¹, M² and M³ are independently hydrogen, fluorine, alkyl having1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least onehydrogen is replaced by fluorine or chlorine; and Sp¹, Sp² and Sp³ areindependently a single bond or alkylene having 1 to 10 carbons, and inthe alkylene, at least one piece of —CH₂— may be replaced by —O—, —COO—,—OCO— or —OCOO—, and at least one piece of —CH₂—CH₂— may be replaced by—CH═CH— or —C≡C—, and in these groups, at least one hydrogen may bereplaced by fluorine or chlorine.
 15. The liquid crystal compositionaccording to claim 12, wherein a proportion of the additive is in therange from 0.03% by weight to 10% by weight.
 16. The liquid crystalcomposition according to claim 5, containing at least one compoundselected from polymerizable compounds represented by formula (5) as anadditive:

wherein, in formula (5), ring G and ring J are independently cyclohexyl,cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl,1,3-dioxane-2-yl, pyrimidine-2-yl or pyridine-2-yl, and in these rings,at least one hydrogen may be replaced by fluorine, chlorine, alkylhaving 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1to 12 carbons in which at least one hydrogen is replaced by fluorine orchlorine; ring I is 1,4-cyclohexylene, 1,4-cyclohexenylene,1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl,naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl,naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl,naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl,1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, and inthese rings, at least one hydrogen may be replaced by fluorine,chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons,or alkyl having 1 to 12 carbons in which at least one hydrogen isreplaced by fluorine or chlorine; Z⁵ and Z⁶ are independently a singlebond or alkylene having 1 to 10 carbons, and in the alkylene, at leastone piece of —CH₂— may be replaced by —O—, —CO—, —COO— or —OCO—, and atleast one piece of —CH₂—CH₂— may be replaced by —CH═CH—, —C(CH₃)═CH—,—CH═C(CH₃)— or —C(CH₃)═C(CH₃)—, and in these groups, at least onehydrogen may be replaced by fluorine or chlorine; P¹, P² and P³ areindependently a polymerizable group; Sp¹, Sp² and Sp³ are independentlya single bond or alkylene having 1 to 10 carbons, and in the alkylene,at least one piece of —CH₂— may be replaced by —O—, —COO—, —OCO— or—OCOO—, and at least one piece of —CH₂—CH₂— may be replaced by —CH═CH—or —C≡C—, and in these groups, at least one hydrogen may be replaced byfluorine or chlorine; d is 0, 1 or 2; and e, f and g are independently0, 1, 2, 3 or 4, and a sum of e, f and g is 1 or more.
 17. The liquidcrystal composition according to claim 11, containing at least onecompound selected from polymerizable compounds represented by formula(5) as an additive:

wherein, in formula (5), ring G and ring J are independently cyclohexyl,cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl,1,3-dioxane-2-yl, pyrimidine-2-yl or pyridine-2-yl, and in these rings,at least one hydrogen may be replaced by fluorine, chlorine, alkylhaving 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1to 12 carbons in which at least one hydrogen is replaced by fluorine orchlorine; ring I is 1,4-cyclohexylene, 1,4-cyclohexenylene,1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl,naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl,naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl,naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl,1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, and inthese rings, at least one hydrogen may be replaced by fluorine,chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons,or alkyl having 1 to 12 carbons in which at least one hydrogen isreplaced by fluorine or chlorine; Z⁵ and Z⁶ are independently a singlebond or alkylene having 1 to 10 carbons, and in the alkylene, at leastone piece of —CH₂— may be replaced by —O—, —CO—, —COO— or —OCO—, and atleast one piece of —CH₂—CH₂— may be replaced by —CH═CH—, —C(CH₃)═CH—,—CH═C(CH₃)— or —C(CH₃)═C(CH₃)—, and in these groups, at least onehydrogen may be replaced by fluorine or chlorine; P′, and P² and P³ areindependently a polymerizable group; Sp¹, Sp² and Sp³ are independentlya single bond or alkylene having 1 to 10 carbons, and in the alkylene,at least one piece of —CH₂— may be replaced by —O—, —COO—, —OCO— or—OCOO—, and at least one piece of —CH₂—CH₂— may be replaced by —CH═CH—or —C≡C—, and in these groups, at least one hydrogen may be replaced byfluorine or chlorine; d is 0, 1 or 2; and e, f and g are independently0, 1, 2, 3 or 4, and a sum of e, f and g is 1 or more.
 18. A liquidcrystal display device, including the liquid crystal compositionaccording to claim
 1. 19. The liquid crystal display device according toclaim 18, wherein an operating mode in the liquid crystal display deviceis an IPS mode, a VA mode, an FFS mode or an FPA mode, and a drivingmode in the liquid crystal display device is an active matrix mode. 20.A polymer sustained alignment mode liquid crystal display device,wherein the liquid crystal display device includes the liquid crystalcomposition according to claim 12, and an additive contained in theliquid crystal composition is polymerized.